NPASS Compound

Structure

CID108721 OpenBabel06191715462D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.1082 5.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6808 5.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5368 3.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7796 4.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 2.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2259 2.4382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7029 3.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8124 4.1230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 2.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2256 1.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 0.9765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6894 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3820 2.9265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4921 4.2986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8451 -0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7111 5.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5365 2.4387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9760 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3825 3.9015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5363 1.4633 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5650 1.4823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5655 -0.5049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3907 5.2683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1794 5.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3523 4.0028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5360 0.4633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 6 0 0 0 18 29 1 6 0 0 0 19 23 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 30 1 6 0 0 0 21 27 1 0 0 0 0 21 31 2 0 0 0 0 22 32 1 0 0 0 0 23 26 1 6 0 0 0 24 27 1 6 0 0 0 25 5 1 6 0 0 0 25 33 1 0 0 0 0 26 34 1 1 0 0 0 27 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.3
Volume:	506.371
LogP:	0.997
LogD:	0.044
LogS:	-3.043
# Rotatable Bonds:	5
TPSA:	158.68
# H-Bond Aceptor:	8
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	5.428
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.546
MDCK Permeability:	6.0743755057046656e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.651
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.449

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.292
Plasma Protein Binding (PPB):	51.57693099975586%
Volume Distribution (VD):	0.505
Pgp-substrate:	26.39192008972168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.739
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.836

ADMET: Excretion

Clearance (CL):	2.656
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.47
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.296
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.512
Carcinogencity:	0.105
Eye Corrosion:	0.005
Eye Irritation:	0.083
Respiratory Toxicity:	0.967

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC108721

Natural Product ID:	NPC108721
*Common Name:**	Polypodin
IUPAC Name:	(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
Synonyms:	Polypodin
Standard InCHIKey:	GMFLGNRCCFYOKL-ACCCYTKYSA-N
Standard InCHI:	InChI=1S/C27H44O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-20,28-30,32-35H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,20+,23+,24+,25+,26+,27+/m0/s1
SMILES:	O[C@H]1C[C@]2(C)[C@H]3CC[C@]4([C@@](C3=CC(=O)[C@@]2(C[C@H]1O)O)(O)CC[C@@H]4[C@]([C@@H](CCC(O)(C)C)O)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502028
PubChem CID:	441833
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)80275-7]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043410]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO14524	Delisea pulchra	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933872]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19467876]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5546	Calycophyllum spruceanum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23189	Achyranthes japonica	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14524	Delisea pulchra	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14017	Bulbine abyssinica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3224	Chloridium virescens	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5051	Lobelia urens	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13240	Pinguipes brasilianus	Species	Pinguipedidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12937	Tithonia pedunculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5546	Calycophyllum spruceanum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8396	Quercus macrocarpa	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9459	Piper hoffmannseggianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21864	Agathis alba	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[448975]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC108721 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1421
0.2-0.3	4436
0.3-0.4	8113
0.4-0.5	12773
0.5-0.6	7170
0.6-0.7	5978
0.7-0.8	2315
0.8-0.85	194
0.85-0.9	37
0.9-0.95	31
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC73300
0.9615	High Similarity	NPC11710
0.9519	High Similarity	NPC217201
0.9423	High Similarity	NPC220229
0.9423	High Similarity	NPC475060
0.9423	High Similarity	NPC83744
0.9423	High Similarity	NPC477916
0.9333	High Similarity	NPC329417
0.9327	High Similarity	NPC48733
0.9327	High Similarity	NPC302607
0.9327	High Similarity	NPC202167
0.9327	High Similarity	NPC85829
0.9327	High Similarity	NPC150531
0.9327	High Similarity	NPC476027
0.9327	High Similarity	NPC149047
0.9327	High Similarity	NPC214264
0.9327	High Similarity	NPC97202
0.9327	High Similarity	NPC319077
0.9327	High Similarity	NPC50692
0.9327	High Similarity	NPC171137
0.9327	High Similarity	NPC49958
0.9327	High Similarity	NPC296945
0.9327	High Similarity	NPC152695
0.9327	High Similarity	NPC260268
0.9286	High Similarity	NPC222688
0.9245	High Similarity	NPC214644
0.9231	High Similarity	NPC204833
0.9231	High Similarity	NPC209502
0.9151	High Similarity	NPC65941
0.9143	High Similarity	NPC257353
0.9135	High Similarity	NPC191892
0.9057	High Similarity	NPC165873
0.9038	High Similarity	NPC477915
0.8991	High Similarity	NPC207251
0.8952	High Similarity	NPC249187
0.8952	High Similarity	NPC247957
0.8909	High Similarity	NPC250109
0.8909	High Similarity	NPC962
0.8909	High Similarity	NPC317210
0.8868	High Similarity	NPC72255
0.8846	High Similarity	NPC154072
0.8839	High Similarity	NPC471854
0.8829	High Similarity	NPC326542
0.8807	High Similarity	NPC76084
0.8785	High Similarity	NPC166607
0.8774	High Similarity	NPC117185
0.8774	High Similarity	NPC311612
0.8772	High Similarity	NPC109973
0.875	High Similarity	NPC266728
0.875	High Similarity	NPC49492
0.8704	High Similarity	NPC185
0.8692	High Similarity	NPC160843
0.8679	High Similarity	NPC87351
0.8679	High Similarity	NPC473424
0.8654	High Similarity	NPC18509
0.8649	High Similarity	NPC280782
0.8611	High Similarity	NPC323834
0.8596	High Similarity	NPC311554
0.8596	High Similarity	NPC257457
0.8558	High Similarity	NPC49371
0.8545	High Similarity	NPC163004
0.8532	High Similarity	NPC58370
0.8532	High Similarity	NPC43285
0.8522	High Similarity	NPC475041
0.8491	Intermediate Similarity	NPC15390
0.8491	Intermediate Similarity	NPC144956
0.8487	Intermediate Similarity	NPC470882
0.8468	Intermediate Similarity	NPC235077
0.8462	Intermediate Similarity	NPC271195
0.8462	Intermediate Similarity	NPC269642
0.8462	Intermediate Similarity	NPC28532
0.8435	Intermediate Similarity	NPC251310
0.8426	Intermediate Similarity	NPC111323
0.8421	Intermediate Similarity	NPC148458
0.839	Intermediate Similarity	NPC473979
0.8378	Intermediate Similarity	NPC470257
0.8365	Intermediate Similarity	NPC111015
0.8365	Intermediate Similarity	NPC196227
0.8365	Intermediate Similarity	NPC196485
0.8365	Intermediate Similarity	NPC245972
0.8349	Intermediate Similarity	NPC149124
0.8349	Intermediate Similarity	NPC75531
0.8347	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC473265
0.8319	Intermediate Similarity	NPC472002
0.8318	Intermediate Similarity	NPC474720
0.8302	Intermediate Similarity	NPC190554
0.8286	Intermediate Similarity	NPC473170
0.8286	Intermediate Similarity	NPC200702
0.8286	Intermediate Similarity	NPC472932
0.8286	Intermediate Similarity	NPC272617
0.8261	Intermediate Similarity	NPC96312
0.8261	Intermediate Similarity	NPC328374
0.8261	Intermediate Similarity	NPC179626
0.8261	Intermediate Similarity	NPC251236
0.8261	Intermediate Similarity	NPC40632
0.8261	Intermediate Similarity	NPC474734
0.8257	Intermediate Similarity	NPC55872
0.8246	Intermediate Similarity	NPC194100
0.8246	Intermediate Similarity	NPC49451
0.8241	Intermediate Similarity	NPC163372
0.8241	Intermediate Similarity	NPC302537
0.823	Intermediate Similarity	NPC472928
0.8214	Intermediate Similarity	NPC87335
0.8214	Intermediate Similarity	NPC471400
0.8211	Intermediate Similarity	NPC471855
0.8208	Intermediate Similarity	NPC249954
0.8208	Intermediate Similarity	NPC471463
0.8198	Intermediate Similarity	NPC472925
0.8198	Intermediate Similarity	NPC144459
0.8197	Intermediate Similarity	NPC470880
0.819	Intermediate Similarity	NPC287343
0.819	Intermediate Similarity	NPC470775
0.819	Intermediate Similarity	NPC103527
0.819	Intermediate Similarity	NPC97908
0.819	Intermediate Similarity	NPC122033
0.819	Intermediate Similarity	NPC472976
0.819	Intermediate Similarity	NPC472977
0.819	Intermediate Similarity	NPC474654
0.819	Intermediate Similarity	NPC239273
0.819	Intermediate Similarity	NPC55296
0.819	Intermediate Similarity	NPC176513
0.819	Intermediate Similarity	NPC470854
0.8182	Intermediate Similarity	NPC137657
0.8182	Intermediate Similarity	NPC473253
0.8182	Intermediate Similarity	NPC28656
0.8174	Intermediate Similarity	NPC473798
0.8173	Intermediate Similarity	NPC155304
0.8173	Intermediate Similarity	NPC116726
0.8173	Intermediate Similarity	NPC168027
0.8173	Intermediate Similarity	NPC185936
0.8167	Intermediate Similarity	NPC473255
0.8165	Intermediate Similarity	NPC119601
0.8165	Intermediate Similarity	NPC204450
0.8165	Intermediate Similarity	NPC195290
0.8165	Intermediate Similarity	NPC308726
0.8158	Intermediate Similarity	NPC474516
0.8158	Intermediate Similarity	NPC100267
0.8158	Intermediate Similarity	NPC475524
0.8158	Intermediate Similarity	NPC71348
0.8148	Intermediate Similarity	NPC316964
0.8148	Intermediate Similarity	NPC110149
0.8148	Intermediate Similarity	NPC127408
0.8148	Intermediate Similarity	NPC291785
0.8148	Intermediate Similarity	NPC327431
0.8148	Intermediate Similarity	NPC83709
0.8136	Intermediate Similarity	NPC112038
0.8136	Intermediate Similarity	NPC472004
0.8131	Intermediate Similarity	NPC474785
0.8131	Intermediate Similarity	NPC474938
0.8131	Intermediate Similarity	NPC170978
0.8125	Intermediate Similarity	NPC295244
0.8125	Intermediate Similarity	NPC472218
0.8125	Intermediate Similarity	NPC168883
0.8125	Intermediate Similarity	NPC472219
0.8125	Intermediate Similarity	NPC472217
0.812	Intermediate Similarity	NPC472397
0.812	Intermediate Similarity	NPC471125
0.812	Intermediate Similarity	NPC472758
0.812	Intermediate Similarity	NPC171905
0.8113	Intermediate Similarity	NPC472485
0.8113	Intermediate Similarity	NPC259286
0.811	Intermediate Similarity	NPC79250
0.811	Intermediate Similarity	NPC290746
0.8108	Intermediate Similarity	NPC51452
0.8108	Intermediate Similarity	NPC196528
0.8108	Intermediate Similarity	NPC60681
0.8103	Intermediate Similarity	NPC270958
0.8099	Intermediate Similarity	NPC225049
0.8099	Intermediate Similarity	NPC293112
0.8095	Intermediate Similarity	NPC472930
0.8095	Intermediate Similarity	NPC109305
0.8095	Intermediate Similarity	NPC69454
0.8095	Intermediate Similarity	NPC472496
0.8091	Intermediate Similarity	NPC236390
0.8091	Intermediate Similarity	NPC251017
0.8091	Intermediate Similarity	NPC26478
0.8087	Intermediate Similarity	NPC202889
0.8087	Intermediate Similarity	NPC7921
0.8087	Intermediate Similarity	NPC208998
0.8083	Intermediate Similarity	NPC43252
0.8083	Intermediate Similarity	NPC135038
0.8083	Intermediate Similarity	NPC67251
0.8077	Intermediate Similarity	NPC473099
0.8077	Intermediate Similarity	NPC48010
0.8077	Intermediate Similarity	NPC134321
0.807	Intermediate Similarity	NPC146945
0.807	Intermediate Similarity	NPC171888
0.8067	Intermediate Similarity	NPC472401
0.8067	Intermediate Similarity	NPC310511
0.8056	Intermediate Similarity	NPC191565
0.8056	Intermediate Similarity	NPC103051
0.8053	Intermediate Similarity	NPC141350
0.8053	Intermediate Similarity	NPC300026
0.8051	Intermediate Similarity	NPC471108
0.8051	Intermediate Similarity	NPC275696
0.8051	Intermediate Similarity	NPC255081
0.8051	Intermediate Similarity	NPC22628
0.8051	Intermediate Similarity	NPC472933
0.8051	Intermediate Similarity	NPC61520

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC108721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1670
0.2-0.3	3983
0.3-0.4	2160
0.4-0.5	642
0.5-0.6	201
0.6-0.7	145
0.7-0.8	93
0.8-0.85	48
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8679	High Similarity	NPD5211	Phase 2
0.8654	High Similarity	NPD4755	Approved
0.8519	High Similarity	NPD5141	Approved
0.8491	Intermediate Similarity	NPD5286	Approved
0.8491	Intermediate Similarity	NPD4700	Approved
0.8491	Intermediate Similarity	NPD4696	Approved
0.8491	Intermediate Similarity	NPD5285	Approved
0.8468	Intermediate Similarity	NPD4634	Approved
0.8378	Intermediate Similarity	NPD6372	Approved
0.8378	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD5225	Approved
0.8333	Intermediate Similarity	NPD5224	Approved
0.8333	Intermediate Similarity	NPD5226	Approved
0.8333	Intermediate Similarity	NPD4633	Approved
0.8273	Intermediate Similarity	NPD6675	Approved
0.8273	Intermediate Similarity	NPD6402	Approved
0.8273	Intermediate Similarity	NPD5739	Approved
0.8273	Intermediate Similarity	NPD4768	Approved
0.8273	Intermediate Similarity	NPD7128	Approved
0.8273	Intermediate Similarity	NPD4767	Approved
0.8257	Intermediate Similarity	NPD5175	Approved
0.8257	Intermediate Similarity	NPD5174	Approved
0.8241	Intermediate Similarity	NPD5223	Approved
0.823	Intermediate Similarity	NPD6650	Approved
0.823	Intermediate Similarity	NPD6649	Approved
0.8158	Intermediate Similarity	NPD8297	Approved
0.8125	Intermediate Similarity	NPD6881	Approved
0.8125	Intermediate Similarity	NPD6899	Approved
0.8125	Intermediate Similarity	NPD4729	Approved
0.8125	Intermediate Similarity	NPD7320	Approved
0.8125	Intermediate Similarity	NPD4730	Approved
0.8091	Intermediate Similarity	NPD4754	Approved
0.8087	Intermediate Similarity	NPD4632	Approved
0.8037	Intermediate Similarity	NPD4697	Phase 3
0.8036	Intermediate Similarity	NPD5701	Approved
0.8036	Intermediate Similarity	NPD5697	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.7983	Intermediate Similarity	NPD6319	Approved
0.7982	Intermediate Similarity	NPD5247	Approved
0.7982	Intermediate Similarity	NPD5249	Phase 3
0.7982	Intermediate Similarity	NPD5251	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7982	Intermediate Similarity	NPD5250	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD5248	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7981	Intermediate Similarity	NPD4753	Phase 2
0.7981	Intermediate Similarity	NPD5328	Approved
0.7965	Intermediate Similarity	NPD5128	Approved
0.7925	Intermediate Similarity	NPD4202	Approved
0.7913	Intermediate Similarity	NPD6869	Approved
0.7913	Intermediate Similarity	NPD8130	Phase 1
0.7913	Intermediate Similarity	NPD6847	Approved
0.7913	Intermediate Similarity	NPD6617	Approved
0.7895	Intermediate Similarity	NPD6013	Approved
0.7895	Intermediate Similarity	NPD6012	Approved
0.7895	Intermediate Similarity	NPD6014	Approved
0.787	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5221	Approved
0.787	Intermediate Similarity	NPD5222	Approved
0.7833	Intermediate Similarity	NPD6059	Approved
0.7833	Intermediate Similarity	NPD6054	Approved
0.783	Intermediate Similarity	NPD6079	Approved
0.7807	Intermediate Similarity	NPD6011	Approved
0.7798	Intermediate Similarity	NPD5173	Approved
0.7778	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD4629	Approved
0.7759	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5215	Approved
0.7759	Intermediate Similarity	NPD5217	Approved
0.7759	Intermediate Similarity	NPD5216	Approved
0.7731	Intermediate Similarity	NPD6009	Approved
0.7705	Intermediate Similarity	NPD6370	Approved
0.7692	Intermediate Similarity	NPD3618	Phase 1
0.7672	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD5135	Approved
0.7672	Intermediate Similarity	NPD5169	Approved
0.7636	Intermediate Similarity	NPD6083	Phase 2
0.7636	Intermediate Similarity	NPD6084	Phase 2
0.7632	Intermediate Similarity	NPD6008	Approved
0.7623	Intermediate Similarity	NPD6016	Approved
0.7623	Intermediate Similarity	NPD6015	Approved
0.7607	Intermediate Similarity	NPD5127	Approved
0.7596	Intermediate Similarity	NPD5329	Approved
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7581	Intermediate Similarity	NPD7492	Approved
0.7561	Intermediate Similarity	NPD5988	Approved
0.752	Intermediate Similarity	NPD7507	Approved
0.752	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD4786	Approved
0.748	Intermediate Similarity	NPD5983	Phase 2
0.748	Intermediate Similarity	NPD7319	Approved
0.746	Intermediate Similarity	NPD7078	Approved
0.746	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD7101	Approved
0.7459	Intermediate Similarity	NPD7100	Approved
0.7417	Intermediate Similarity	NPD5167	Approved
0.7414	Intermediate Similarity	NPD6412	Phase 2
0.7411	Intermediate Similarity	NPD5696	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7381	Intermediate Similarity	NPD6336	Discontinued
0.7377	Intermediate Similarity	NPD6335	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7640	Approved
0.7345	Intermediate Similarity	NPD7639	Approved
0.7339	Intermediate Similarity	NPD6909	Approved
0.7339	Intermediate Similarity	NPD6908	Approved
0.7317	Intermediate Similarity	NPD7516	Approved
0.7308	Intermediate Similarity	NPD3667	Approved
0.7308	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD4223	Phase 3
0.7297	Intermediate Similarity	NPD5695	Phase 3
0.7295	Intermediate Similarity	NPD6317	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7266	Intermediate Similarity	NPD6033	Approved
0.7257	Intermediate Similarity	NPD7638	Approved
0.7236	Intermediate Similarity	NPD6314	Approved
0.7236	Intermediate Similarity	NPD7327	Approved
0.7236	Intermediate Similarity	NPD6313	Approved
0.7236	Intermediate Similarity	NPD7328	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5168	Approved
0.72	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5690	Phase 2
0.7196	Intermediate Similarity	NPD4694	Approved
0.7196	Intermediate Similarity	NPD5279	Phase 3
0.7196	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5280	Approved
0.7177	Intermediate Similarity	NPD4522	Approved
0.713	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD8328	Phase 3
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7027	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD5284	Approved
0.7027	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7524	Approved
0.6952	Remote Similarity	NPD7525	Registered
0.6935	Remote Similarity	NPD6868	Approved
0.6929	Remote Similarity	NPD8379	Approved
0.6929	Remote Similarity	NPD8296	Approved
0.6929	Remote Similarity	NPD8033	Approved
0.6929	Remote Similarity	NPD8378	Approved
0.6929	Remote Similarity	NPD8380	Approved
0.6929	Remote Similarity	NPD8335	Approved
0.6916	Remote Similarity	NPD4788	Approved
0.6909	Remote Similarity	NPD5737	Approved
0.6909	Remote Similarity	NPD6672	Approved
0.6881	Remote Similarity	NPD6684	Approved
0.6881	Remote Similarity	NPD7521	Approved
0.6881	Remote Similarity	NPD6409	Approved
0.6881	Remote Similarity	NPD5330	Approved
0.6881	Remote Similarity	NPD7146	Approved
0.6881	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.687	Remote Similarity	NPD7902	Approved
0.6852	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3668	Phase 3
0.685	Remote Similarity	NPD8377	Approved
0.685	Remote Similarity	NPD8294	Approved
0.681	Remote Similarity	NPD4225	Approved
0.6797	Remote Similarity	NPD7503	Approved
0.6797	Remote Similarity	NPD6921	Approved
0.6792	Remote Similarity	NPD6930	Phase 2
0.6792	Remote Similarity	NPD6931	Approved
0.6792	Remote Similarity	NPD4695	Discontinued
0.678	Remote Similarity	NPD5091	Approved
0.678	Remote Similarity	NPD7632	Discontinued
0.6777	Remote Similarity	NPD6686	Approved
0.6762	Remote Similarity	NPD3617	Approved
0.6759	Remote Similarity	NPD6695	Phase 3
0.6757	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD7748	Approved
0.6746	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4519	Discontinued
0.6727	Remote Similarity	NPD6098	Approved
0.6727	Remote Similarity	NPD4623	Approved
0.6726	Remote Similarity	NPD6050	Approved
0.6721	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6929	Approved
0.6698	Remote Similarity	NPD4195	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data