NPASS Compound

Structure

CID160209 OpenBabel06191715532D 31 33 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 7 29 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 22 24 2 0 0 0 0 23 5 1 1 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 29 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 27 30 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.4
Volume:	505.284
LogP:	8.158
LogD:	5.743
LogS:	-6.864
# Rotatable Bonds:	7
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	4.601
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	8.638428880658466e-06
Pgp-inhibitor:	0.026
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.322
Plasma Protein Binding (PPB):	92.45172882080078%
Volume Distribution (VD):	4.935
Pgp-substrate:	1.4262911081314087%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.259
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.622

ADMET: Excretion

Clearance (CL):	14.421
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.754
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.946
Carcinogencity:	0.181
Eye Corrosion:	0.1
Eye Irritation:	0.478
Respiratory Toxicity:	0.288

Download Data

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

Natural Product: NPC160209

Natural Product ID:	NPC160209
*Common Name:**	Isohelianol
IUPAC Name:	3-[(3S,3aS,5aS,6S,9aS,9bR)-3a,5a,9b-trimethyl-3-[(2R)-6-methylhept-5-en-2-yl]-7-propan-2-ylidene-2,3,4,5,6,8,9,9a-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propan-1-ol
Synonyms:	Isohelianol
Standard InCHIKey:	PDGUDHUKTNJAMM-GSHMMLCQSA-N
Standard InCHI:	InChI=1S/C30H52O/c1-21(2)11-9-12-23(5)25-16-17-30(8)27-15-14-24(22(3)4)26(13-10-20-31)28(27,6)18-19-29(25,30)7/h11,23,25-27,31H,9-10,12-20H2,1-8H3/t23-,25+,26-,27+,28+,29+,30-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@@H]1CC[C@]2(C)[C@H]3CCC(=C(C)C)[C@@H](CCCO)[C@]3(C)CC[C@@]12C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463551
PubChem CID:	10455281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043410]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1048	Ajuga reptans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8432	Haminoea orbignyana	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3867	Smallanthus glabratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14477	Comamonas testosteroni	Species	Comamonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24071	Girgensohnia diptera	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1048	Ajuga reptans	Species	Lamiaceae	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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[569001]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[569001]
NPT2	Others	Unspecified		Activity	=	25.8	%	PMID[569001]
NPT2	Others	Unspecified		Activity	=	72.4	%	PMID[569001]
NPT2	Others	Unspecified		Activity	=	95.7	%	PMID[569001]

☑ 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 NPC160209 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	137
0.1-0.2	1485
0.2-0.3	11475
0.3-0.4	13497
0.4-0.5	6517
0.5-0.6	5572
0.6-0.7	3053
0.7-0.8	769
0.8-0.85	106
0.85-0.9	58
0.9-0.95	27
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC304309
0.913	High Similarity	NPC136188
0.913	High Similarity	NPC22105
0.913	High Similarity	NPC285893
0.913	High Similarity	NPC162742
0.913	High Similarity	NPC141071
0.913	High Similarity	NPC134847
0.913	High Similarity	NPC471723
0.913	High Similarity	NPC28657
0.913	High Similarity	NPC230301
0.913	High Similarity	NPC257347
0.913	High Similarity	NPC288035
0.9118	High Similarity	NPC474140
0.9	High Similarity	NPC300324
0.9	High Similarity	NPC247325
0.9	High Similarity	NPC321381
0.9	High Similarity	NPC134330
0.9	High Similarity	NPC189883
0.9	High Similarity	NPC107059
0.9	High Similarity	NPC113733
0.9	High Similarity	NPC237460
0.9	High Similarity	NPC244488
0.9	High Similarity	NPC129165
0.9	High Similarity	NPC321016
0.9	High Similarity	NPC240604
0.8939	High Similarity	NPC197805
0.8923	High Similarity	NPC27243
0.8923	High Similarity	NPC476737
0.8873	High Similarity	NPC155986
0.8873	High Similarity	NPC318495
0.8873	High Similarity	NPC34019
0.8873	High Similarity	NPC198968
0.8857	High Similarity	NPC471468
0.8841	High Similarity	NPC474743
0.8824	High Similarity	NPC475728
0.8788	High Similarity	NPC286669
0.8788	High Similarity	NPC149680
0.8788	High Similarity	NPC476039
0.8788	High Similarity	NPC222366
0.875	High Similarity	NPC477514
0.875	High Similarity	NPC167037
0.875	High Similarity	NPC473943
0.875	High Similarity	NPC18603
0.875	High Similarity	NPC65897
0.875	High Similarity	NPC76931
0.875	High Similarity	NPC85346
0.875	High Similarity	NPC285761
0.875	High Similarity	NPC6978
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.875	High Similarity	NPC302041
0.875	High Similarity	NPC244385
0.875	High Similarity	NPC474216
0.875	High Similarity	NPC138621
0.875	High Similarity	NPC307965
0.8732	High Similarity	NPC202642
0.8732	High Similarity	NPC46160
0.8732	High Similarity	NPC470362
0.8714	High Similarity	NPC329090
0.8714	High Similarity	NPC27395
0.8676	High Similarity	NPC167272
0.8676	High Similarity	NPC269877
0.8657	High Similarity	NPC68703
0.8657	High Similarity	NPC69649
0.863	High Similarity	NPC328714
0.863	High Similarity	NPC209430
0.863	High Similarity	NPC80530
0.863	High Similarity	NPC47982
0.863	High Similarity	NPC28862
0.863	High Similarity	NPC273410
0.863	High Similarity	NPC143182
0.863	High Similarity	NPC1319
0.863	High Similarity	NPC84694
0.863	High Similarity	NPC81306
0.863	High Similarity	NPC109546
0.863	High Similarity	NPC30986
0.8611	High Similarity	NPC214570
0.8592	High Similarity	NPC118508
0.8592	High Similarity	NPC319090
0.8592	High Similarity	NPC322353
0.8592	High Similarity	NPC328104
0.8592	High Similarity	NPC121744
0.8551	High Similarity	NPC9161
0.8551	High Similarity	NPC49422
0.8529	High Similarity	NPC216460
0.8529	High Similarity	NPC208999
0.8529	High Similarity	NPC32055
0.8514	High Similarity	NPC209944
0.8514	High Similarity	NPC26117
0.8514	High Similarity	NPC322313
0.8514	High Similarity	NPC164840
0.8514	High Similarity	NPC236237
0.8514	High Similarity	NPC234193
0.8514	High Similarity	NPC241290
0.8514	High Similarity	NPC102253
0.8514	High Similarity	NPC236112
0.8514	High Similarity	NPC13554
0.8493	Intermediate Similarity	NPC275910
0.8493	Intermediate Similarity	NPC312328
0.8493	Intermediate Similarity	NPC205455
0.8493	Intermediate Similarity	NPC186191
0.8472	Intermediate Similarity	NPC73875
0.8472	Intermediate Similarity	NPC315261
0.8472	Intermediate Similarity	NPC96319
0.8462	Intermediate Similarity	NPC147524
0.8451	Intermediate Similarity	NPC469534
0.8451	Intermediate Similarity	NPC469533
0.8451	Intermediate Similarity	NPC469593
0.8429	Intermediate Similarity	NPC111234
0.8429	Intermediate Similarity	NPC167706
0.84	Intermediate Similarity	NPC264245
0.84	Intermediate Similarity	NPC47761
0.84	Intermediate Similarity	NPC474731
0.84	Intermediate Similarity	NPC474531
0.84	Intermediate Similarity	NPC474759
0.84	Intermediate Similarity	NPC474752
0.84	Intermediate Similarity	NPC474683
0.84	Intermediate Similarity	NPC209620
0.84	Intermediate Similarity	NPC82986
0.84	Intermediate Similarity	NPC470383
0.84	Intermediate Similarity	NPC23852
0.84	Intermediate Similarity	NPC7505
0.8358	Intermediate Similarity	NPC163678
0.8358	Intermediate Similarity	NPC477009
0.8358	Intermediate Similarity	NPC238352
0.831	Intermediate Similarity	NPC201373
0.831	Intermediate Similarity	NPC471799
0.831	Intermediate Similarity	NPC195489
0.831	Intermediate Similarity	NPC182717
0.8289	Intermediate Similarity	NPC30166
0.8289	Intermediate Similarity	NPC5985
0.8289	Intermediate Similarity	NPC470614
0.8289	Intermediate Similarity	NPC49964
0.8289	Intermediate Similarity	NPC296701
0.8289	Intermediate Similarity	NPC1272
0.8289	Intermediate Similarity	NPC470049
0.8289	Intermediate Similarity	NPC218616
0.8289	Intermediate Similarity	NPC189972
0.8289	Intermediate Similarity	NPC101462
0.8289	Intermediate Similarity	NPC50964
0.8286	Intermediate Similarity	NPC145498
0.8286	Intermediate Similarity	NPC34834
0.8286	Intermediate Similarity	NPC45296
0.8243	Intermediate Similarity	NPC318136
0.8209	Intermediate Similarity	NPC225415
0.8209	Intermediate Similarity	NPC309300
0.8194	Intermediate Similarity	NPC5046
0.8194	Intermediate Similarity	NPC476366
0.8194	Intermediate Similarity	NPC196358
0.8194	Intermediate Similarity	NPC192638
0.8194	Intermediate Similarity	NPC145552
0.8194	Intermediate Similarity	NPC49168
0.8194	Intermediate Similarity	NPC471797
0.8194	Intermediate Similarity	NPC100334
0.8194	Intermediate Similarity	NPC62657
0.8194	Intermediate Similarity	NPC201048
0.8194	Intermediate Similarity	NPC254509
0.8194	Intermediate Similarity	NPC25511
0.8182	Intermediate Similarity	NPC477818
0.8182	Intermediate Similarity	NPC207013
0.8182	Intermediate Similarity	NPC474634
0.8182	Intermediate Similarity	NPC317458
0.8182	Intermediate Similarity	NPC113978
0.8182	Intermediate Similarity	NPC110778
0.8182	Intermediate Similarity	NPC475789
0.8169	Intermediate Similarity	NPC164045
0.8169	Intermediate Similarity	NPC242001
0.8158	Intermediate Similarity	NPC70927
0.8154	Intermediate Similarity	NPC5698
0.8133	Intermediate Similarity	NPC472463
0.8116	Intermediate Similarity	NPC171225
0.8082	Intermediate Similarity	NPC103822
0.8082	Intermediate Similarity	NPC185536
0.8082	Intermediate Similarity	NPC240235
0.8082	Intermediate Similarity	NPC32832
0.8082	Intermediate Similarity	NPC70982
0.8082	Intermediate Similarity	NPC178383
0.8082	Intermediate Similarity	NPC212879
0.8082	Intermediate Similarity	NPC230704
0.8082	Intermediate Similarity	NPC3403
0.8082	Intermediate Similarity	NPC200243
0.8082	Intermediate Similarity	NPC231256
0.8082	Intermediate Similarity	NPC104387
0.8077	Intermediate Similarity	NPC476038
0.8077	Intermediate Similarity	NPC124172
0.8077	Intermediate Similarity	NPC474047
0.8077	Intermediate Similarity	NPC209802
0.8077	Intermediate Similarity	NPC185568
0.8077	Intermediate Similarity	NPC82902
0.8077	Intermediate Similarity	NPC478102
0.8077	Intermediate Similarity	NPC221758
0.8077	Intermediate Similarity	NPC472265
0.8077	Intermediate Similarity	NPC85774
0.8077	Intermediate Similarity	NPC59453
0.8077	Intermediate Similarity	NPC205845
0.8077	Intermediate Similarity	NPC470077
0.8077	Intermediate Similarity	NPC214043
0.8077	Intermediate Similarity	NPC194937
0.8077	Intermediate Similarity	NPC33913
0.8056	Intermediate Similarity	NPC68443

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 NPC160209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1784
0.2-0.3	4645
0.3-0.4	1814
0.4-0.5	390
0.5-0.6	152
0.6-0.7	151
0.7-0.8	53
0.8-0.85	13
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD6942	Approved
0.913	High Similarity	NPD7339	Approved
0.8714	High Similarity	NPD6926	Approved
0.8714	High Similarity	NPD6924	Approved
0.8696	High Similarity	NPD4243	Approved
0.8676	High Similarity	NPD6923	Approved
0.8676	High Similarity	NPD6922	Approved
0.8551	High Similarity	NPD7143	Approved
0.8551	High Similarity	NPD7144	Approved
0.8514	High Similarity	NPD7525	Registered
0.8472	Intermediate Similarity	NPD6933	Approved
0.8472	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD4784	Approved
0.8451	Intermediate Similarity	NPD4785	Approved
0.8429	Intermediate Similarity	NPD7150	Approved
0.8429	Intermediate Similarity	NPD7151	Approved
0.8429	Intermediate Similarity	NPD7152	Approved
0.8133	Intermediate Similarity	NPD6929	Approved
0.8082	Intermediate Similarity	NPD4190	Phase 3
0.8082	Intermediate Similarity	NPD5275	Approved
0.8077	Intermediate Similarity	NPD4786	Approved
0.8026	Intermediate Similarity	NPD6931	Approved
0.8026	Intermediate Similarity	NPD6930	Phase 2
0.7867	Intermediate Similarity	NPD6925	Approved
0.7867	Intermediate Similarity	NPD5776	Phase 2
0.7867	Intermediate Similarity	NPD6932	Approved
0.7821	Intermediate Similarity	NPD3667	Approved
0.7792	Intermediate Similarity	NPD7509	Discontinued
0.7763	Intermediate Similarity	NPD7145	Approved
0.7722	Intermediate Similarity	NPD6695	Phase 3
0.7662	Intermediate Similarity	NPD6683	Phase 2
0.7662	Intermediate Similarity	NPD4195	Approved
0.7662	Intermediate Similarity	NPD7645	Phase 2
0.7625	Intermediate Similarity	NPD3133	Approved
0.7625	Intermediate Similarity	NPD3666	Approved
0.7625	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3665	Phase 1
0.759	Intermediate Similarity	NPD5328	Approved
0.7564	Intermediate Similarity	NPD7514	Phase 3
0.7561	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6893	Approved
0.7468	Intermediate Similarity	NPD6902	Approved
0.7439	Intermediate Similarity	NPD3618	Phase 1
0.7412	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD4753	Phase 2
0.7375	Intermediate Similarity	NPD4221	Approved
0.7375	Intermediate Similarity	NPD4223	Phase 3
0.7349	Intermediate Similarity	NPD7750	Discontinued
0.7349	Intermediate Similarity	NPD7524	Approved
0.7342	Intermediate Similarity	NPD7332	Phase 2
0.7342	Intermediate Similarity	NPD4748	Discontinued
0.7317	Intermediate Similarity	NPD5329	Approved
0.7284	Intermediate Similarity	NPD4788	Approved
0.725	Intermediate Similarity	NPD6898	Phase 1
0.7229	Intermediate Similarity	NPD5279	Phase 3
0.7195	Intermediate Similarity	NPD4197	Approved
0.7126	Intermediate Similarity	NPD6399	Phase 3
0.7126	Intermediate Similarity	NPD4202	Approved
0.7108	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4688	Approved
0.7024	Intermediate Similarity	NPD5205	Approved
0.7024	Intermediate Similarity	NPD4689	Approved
0.7024	Intermediate Similarity	NPD4138	Approved
0.7024	Intermediate Similarity	NPD4693	Phase 3
0.7024	Intermediate Similarity	NPD4690	Approved
0.7015	Intermediate Similarity	NPD342	Phase 1
0.7011	Intermediate Similarity	NPD7087	Discontinued
0.7	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD6083	Phase 2
0.6988	Remote Similarity	NPD3668	Phase 3
0.6966	Remote Similarity	NPD5210	Approved
0.6966	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD8264	Approved
0.6889	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5222	Approved
0.6889	Remote Similarity	NPD5221	Approved
0.6875	Remote Similarity	NPD3617	Approved
0.686	Remote Similarity	NPD6672	Approved
0.686	Remote Similarity	NPD4723	Approved
0.686	Remote Similarity	NPD4722	Approved
0.686	Remote Similarity	NPD5737	Approved
0.6849	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7334	Approved
0.6824	Remote Similarity	NPD7521	Approved
0.6824	Remote Similarity	NPD5690	Phase 2
0.6824	Remote Similarity	NPD6409	Approved
0.6824	Remote Similarity	NPD4694	Approved
0.6824	Remote Similarity	NPD6684	Approved
0.6824	Remote Similarity	NPD7146	Approved
0.6824	Remote Similarity	NPD5330	Approved
0.6824	Remote Similarity	NPD5280	Approved
0.6813	Remote Similarity	NPD5173	Approved
0.6813	Remote Similarity	NPD4755	Approved
0.68	Remote Similarity	NPD6705	Phase 1
0.6782	Remote Similarity	NPD6051	Approved
0.6739	Remote Similarity	NPD7638	Approved
0.6711	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6629	Remote Similarity	NPD7637	Suspended
0.6629	Remote Similarity	NPD7515	Phase 2
0.6628	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6098	Approved
0.6627	Remote Similarity	NPD4139	Approved
0.6627	Remote Similarity	NPD4692	Approved
0.6623	Remote Similarity	NPD6939	Phase 2
0.6623	Remote Similarity	NPD4747	Approved
0.6623	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4789	Approved
0.6623	Remote Similarity	NPD4787	Phase 1
0.6596	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD5695	Phase 3
0.6579	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5290	Discontinued
0.6559	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5224	Approved
0.6526	Remote Similarity	NPD5225	Approved
0.6526	Remote Similarity	NPD4633	Approved
0.6526	Remote Similarity	NPD5226	Approved
0.6526	Remote Similarity	NPD5211	Phase 2
0.6517	Remote Similarity	NPD7136	Phase 2
0.6506	Remote Similarity	NPD4695	Discontinued
0.6495	Remote Similarity	NPD5739	Approved
0.6495	Remote Similarity	NPD6675	Approved
0.6495	Remote Similarity	NPD6402	Approved
0.6495	Remote Similarity	NPD7128	Approved
0.6494	Remote Similarity	NPD4137	Phase 3
0.6463	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4754	Approved
0.6458	Remote Similarity	NPD5174	Approved
0.6458	Remote Similarity	NPD5175	Approved
0.6444	Remote Similarity	NPD8034	Phase 2
0.6444	Remote Similarity	NPD5281	Approved
0.6444	Remote Similarity	NPD5284	Approved
0.6444	Remote Similarity	NPD8035	Phase 2
0.6438	Remote Similarity	NPD368	Approved
0.6437	Remote Similarity	NPD4519	Discontinued
0.6437	Remote Similarity	NPD4623	Approved
0.6429	Remote Similarity	NPD4219	Approved
0.642	Remote Similarity	NPD1346	Approved
0.641	Remote Similarity	NPD4245	Approved
0.641	Remote Similarity	NPD4244	Approved
0.641	Remote Similarity	NPD4691	Approved
0.6404	Remote Similarity	NPD6904	Approved
0.6404	Remote Similarity	NPD6080	Approved
0.6404	Remote Similarity	NPD6673	Approved
0.6392	Remote Similarity	NPD5141	Approved
0.6375	Remote Similarity	NPD5733	Approved
0.6375	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD7320	Approved
0.6364	Remote Similarity	NPD6899	Approved
0.6353	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4096	Approved
0.6327	Remote Similarity	NPD4767	Approved
0.6327	Remote Similarity	NPD4768	Approved
0.6304	Remote Similarity	NPD7748	Approved
0.6304	Remote Similarity	NPD5771	Approved
0.63	Remote Similarity	NPD6373	Approved
0.63	Remote Similarity	NPD6372	Approved
0.6292	Remote Similarity	NPD5208	Approved
0.6282	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD3698	Phase 2
0.6282	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5701	Approved
0.6263	Remote Similarity	NPD5697	Approved
0.6263	Remote Similarity	NPD6412	Phase 2
0.6238	Remote Similarity	NPD7102	Approved
0.6238	Remote Similarity	NPD6883	Approved
0.6238	Remote Similarity	NPD7290	Approved
0.6237	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6117	Approved
0.62	Remote Similarity	NPD5168	Approved
0.62	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD4730	Approved
0.62	Remote Similarity	NPD4729	Approved
0.62	Remote Similarity	NPD5128	Approved
0.6196	Remote Similarity	NPD5133	Approved
0.6176	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8130	Phase 1
0.6176	Remote Similarity	NPD6650	Approved
0.6176	Remote Similarity	NPD6649	Approved
0.6176	Remote Similarity	NPD6869	Approved
0.6176	Remote Similarity	NPD6847	Approved
0.6176	Remote Similarity	NPD6617	Approved
0.6173	Remote Similarity	NPD4058	Approved
0.6173	Remote Similarity	NPD4687	Approved
0.6154	Remote Similarity	NPD5360	Phase 3
0.6154	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6404	Discontinued

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