NPASS Compound

Structure

CID184555 OpenBabel06191715562D 30 34 0 0 1 0 0 0 0 0999 V2000 4.2576 0.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6447 1.7666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6147 1.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5359 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8455 1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2264 2.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3814 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3814 2.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4686 0.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -0.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0717 0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2269 1.4648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6910 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6910 0.9763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0116 0.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3814 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8455 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5365 1.4645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4877 -1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7108 -1.9637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9816 0.6725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6704 1.9645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4386 -0.0150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 9 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 30 1 0 0 0 0 14 22 1 0 0 0 0 14 25 2 0 0 0 0 15 17 1 0 0 0 0 16 26 1 6 0 0 0 17 21 1 6 0 0 0 18 19 1 0 0 0 0 18 22 1 6 0 0 0 19 24 1 1 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 24 1 6 0 0 0 22 23 1 6 0 0 0 23 28 1 6 0 0 0 24 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	423.073
LogP:	1.003
LogD:	0.918
LogS:	-3.038
# Rotatable Bonds:	2
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	4.729
Fsp3:	0.75
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:	-5.56
MDCK Permeability:	1.3737493645749055e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.565
Plasma Protein Binding (PPB):	59.9615478515625%
Volume Distribution (VD):	0.415
Pgp-substrate:	24.408018112182617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.19
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	8.012
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.516
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.904
Carcinogencity:	0.943
Eye Corrosion:	0.029
Eye Irritation:	0.048
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC184555

Natural Product ID:	NPC184555
*Common Name:**	3,5,14-Trihydroxy-13-Methyl-17-(6-Oxo-6H-Pyran-3-Yl)-Hexadecahydro-Cyclopenta[A]Phenanthrene-10-Carbaldehyde
IUPAC Name:	(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:
Standard InCHIKey:	TVKPTWJPKVSGJB-XHCIOXAKSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1
SMILES:	C[C@@]12CC[C@H]3[C@@H](CC[C@@]4(C[C@H](CC[C@]34C=O)O)O)[C@]2(CC[C@@H]1c1ccc(=O)oc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2068960
PubChem CID:	259577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO25922	Hedyotis verticillata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7938277]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25922	Hedyotis verticillata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2208	Doronicum hungaricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	0.00016	ug.mL-1	PMID[537155]
NPT2	Others	Unspecified		IC50	=	0.00053	ug.mL-1	PMID[537155]

☑ 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 NPC184555 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	354
0.1-0.2	1436
0.2-0.3	2725
0.3-0.4	5040
0.4-0.5	10276
0.5-0.6	9847
0.6-0.7	9125
0.7-0.8	3471
0.8-0.85	313
0.85-0.9	53
0.9-0.95	29
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC55602
0.9478	High Similarity	NPC233041
0.9455	High Similarity	NPC73050
0.9123	High Similarity	NPC146786
0.9016	High Similarity	NPC248703
0.9	High Similarity	NPC304276
0.9	High Similarity	NPC137462
0.8966	High Similarity	NPC41123
0.8966	High Similarity	NPC114939
0.8966	High Similarity	NPC145074
0.8947	High Similarity	NPC72772
0.8947	High Similarity	NPC469794
0.8871	High Similarity	NPC62172
0.8871	High Similarity	NPC289700
0.8843	High Similarity	NPC221414
0.8839	High Similarity	NPC12795
0.8839	High Similarity	NPC16270
0.875	High Similarity	NPC159499
0.873	High Similarity	NPC75616
0.8684	High Similarity	NPC44537
0.8649	High Similarity	NPC189863
0.8636	High Similarity	NPC171014
0.8609	High Similarity	NPC154815
0.8609	High Similarity	NPC171126
0.8571	High Similarity	NPC263729
0.8522	High Similarity	NPC247760
0.8509	High Similarity	NPC103491
0.8496	Intermediate Similarity	NPC275060
0.8487	Intermediate Similarity	NPC476962
0.8482	Intermediate Similarity	NPC266570
0.8482	Intermediate Similarity	NPC295843
0.8435	Intermediate Similarity	NPC183603
0.8421	Intermediate Similarity	NPC257082
0.8421	Intermediate Similarity	NPC285298
0.8421	Intermediate Similarity	NPC75389
0.8407	Intermediate Similarity	NPC79298
0.8407	Intermediate Similarity	NPC179380
0.8407	Intermediate Similarity	NPC43063
0.84	Intermediate Similarity	NPC155529
0.839	Intermediate Similarity	NPC476959
0.8305	Intermediate Similarity	NPC196931
0.8305	Intermediate Similarity	NPC476963
0.8279	Intermediate Similarity	NPC6193
0.8279	Intermediate Similarity	NPC11895
0.8279	Intermediate Similarity	NPC204812
0.8276	Intermediate Similarity	NPC474315
0.8264	Intermediate Similarity	NPC46570
0.825	Intermediate Similarity	NPC213761
0.825	Intermediate Similarity	NPC35171
0.824	Intermediate Similarity	NPC471361
0.824	Intermediate Similarity	NPC231529
0.824	Intermediate Similarity	NPC251866
0.824	Intermediate Similarity	NPC89514
0.824	Intermediate Similarity	NPC471358
0.824	Intermediate Similarity	NPC284406
0.824	Intermediate Similarity	NPC70542
0.824	Intermediate Similarity	NPC9499
0.824	Intermediate Similarity	NPC219085
0.824	Intermediate Similarity	NPC6108
0.824	Intermediate Similarity	NPC469754
0.824	Intermediate Similarity	NPC471360
0.824	Intermediate Similarity	NPC469751
0.824	Intermediate Similarity	NPC471359
0.824	Intermediate Similarity	NPC469752
0.824	Intermediate Similarity	NPC197707
0.824	Intermediate Similarity	NPC86159
0.824	Intermediate Similarity	NPC471352
0.824	Intermediate Similarity	NPC469753
0.824	Intermediate Similarity	NPC10823
0.824	Intermediate Similarity	NPC180079
0.824	Intermediate Similarity	NPC469755
0.824	Intermediate Similarity	NPC17896
0.8235	Intermediate Similarity	NPC474518
0.8235	Intermediate Similarity	NPC239273
0.823	Intermediate Similarity	NPC201763
0.822	Intermediate Similarity	NPC470953
0.8214	Intermediate Similarity	NPC193934
0.8214	Intermediate Similarity	NPC271980
0.8211	Intermediate Similarity	NPC32868
0.8211	Intermediate Similarity	NPC81736
0.8211	Intermediate Similarity	NPC172154
0.8211	Intermediate Similarity	NPC241456
0.8205	Intermediate Similarity	NPC476163
0.8205	Intermediate Similarity	NPC277769
0.8205	Intermediate Similarity	NPC4573
0.8205	Intermediate Similarity	NPC90952
0.8203	Intermediate Similarity	NPC158350
0.8197	Intermediate Similarity	NPC107493
0.8197	Intermediate Similarity	NPC170538
0.819	Intermediate Similarity	NPC478209
0.8182	Intermediate Similarity	NPC112936
0.8182	Intermediate Similarity	NPC257610
0.8174	Intermediate Similarity	NPC177064
0.8174	Intermediate Similarity	NPC163216
0.8167	Intermediate Similarity	NPC16701
0.8158	Intermediate Similarity	NPC34768
0.8145	Intermediate Similarity	NPC293112
0.8142	Intermediate Similarity	NPC112009
0.8142	Intermediate Similarity	NPC312900
0.814	Intermediate Similarity	NPC127656
0.8136	Intermediate Similarity	NPC122056
0.8136	Intermediate Similarity	NPC241977
0.813	Intermediate Similarity	NPC469789
0.813	Intermediate Similarity	NPC473979
0.8125	Intermediate Similarity	NPC282524
0.8108	Intermediate Similarity	NPC57079
0.8108	Intermediate Similarity	NPC108368
0.8099	Intermediate Similarity	NPC270850
0.8099	Intermediate Similarity	NPC305260
0.8099	Intermediate Similarity	NPC476960
0.8099	Intermediate Similarity	NPC278681
0.8099	Intermediate Similarity	NPC264954
0.8087	Intermediate Similarity	NPC330011
0.8087	Intermediate Similarity	NPC329048
0.8083	Intermediate Similarity	NPC185287
0.8083	Intermediate Similarity	NPC55296
0.8083	Intermediate Similarity	NPC157380
0.808	Intermediate Similarity	NPC469757
0.808	Intermediate Similarity	NPC117702
0.808	Intermediate Similarity	NPC471357
0.808	Intermediate Similarity	NPC179412
0.808	Intermediate Similarity	NPC146456
0.808	Intermediate Similarity	NPC471356
0.807	Intermediate Similarity	NPC165969
0.8067	Intermediate Similarity	NPC238667
0.8067	Intermediate Similarity	NPC147912
0.8067	Intermediate Similarity	NPC67259
0.8065	Intermediate Similarity	NPC8374
0.8065	Intermediate Similarity	NPC8369
0.8051	Intermediate Similarity	NPC475970
0.8051	Intermediate Similarity	NPC69291
0.8049	Intermediate Similarity	NPC269642
0.8047	Intermediate Similarity	NPC116075
0.8047	Intermediate Similarity	NPC32793
0.8047	Intermediate Similarity	NPC146857
0.8047	Intermediate Similarity	NPC469749
0.8047	Intermediate Similarity	NPC247190
0.8036	Intermediate Similarity	NPC35751
0.8034	Intermediate Similarity	NPC179642
0.8033	Intermediate Similarity	NPC79579
0.8033	Intermediate Similarity	NPC476961
0.8033	Intermediate Similarity	NPC474370
0.8017	Intermediate Similarity	NPC153440
0.8017	Intermediate Similarity	NPC476802
0.8017	Intermediate Similarity	NPC113448
0.8017	Intermediate Similarity	NPC472825
0.8017	Intermediate Similarity	NPC89171
0.8	Intermediate Similarity	NPC190286
0.8	Intermediate Similarity	NPC250556
0.8	Intermediate Similarity	NPC473635
0.8	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC469750
0.7984	Intermediate Similarity	NPC329636
0.7983	Intermediate Similarity	NPC478212
0.7982	Intermediate Similarity	NPC72151
0.7982	Intermediate Similarity	NPC10232
0.7982	Intermediate Similarity	NPC189588
0.7982	Intermediate Similarity	NPC180204
0.7982	Intermediate Similarity	NPC329345
0.7982	Intermediate Similarity	NPC187302
0.7982	Intermediate Similarity	NPC475526
0.7982	Intermediate Similarity	NPC120321
0.7982	Intermediate Similarity	NPC473283
0.7982	Intermediate Similarity	NPC196471
0.7982	Intermediate Similarity	NPC97487
0.7967	Intermediate Similarity	NPC312481
0.7967	Intermediate Similarity	NPC67569
0.7965	Intermediate Similarity	NPC471412
0.7965	Intermediate Similarity	NPC168319
0.7965	Intermediate Similarity	NPC194028
0.7951	Intermediate Similarity	NPC230513
0.7951	Intermediate Similarity	NPC5292
0.7951	Intermediate Similarity	NPC475041
0.7949	Intermediate Similarity	NPC475065
0.7946	Intermediate Similarity	NPC477854
0.7937	Intermediate Similarity	NPC287423
0.7934	Intermediate Similarity	NPC476965
0.7934	Intermediate Similarity	NPC475809
0.7934	Intermediate Similarity	NPC470959
0.7934	Intermediate Similarity	NPC470492
0.7934	Intermediate Similarity	NPC140055
0.7934	Intermediate Similarity	NPC134430
0.7934	Intermediate Similarity	NPC167606
0.7934	Intermediate Similarity	NPC286528
0.7934	Intermediate Similarity	NPC20302
0.7931	Intermediate Similarity	NPC302788
0.7931	Intermediate Similarity	NPC64844
0.7931	Intermediate Similarity	NPC42847
0.7928	Intermediate Similarity	NPC471153
0.7923	Intermediate Similarity	NPC194716
0.792	Intermediate Similarity	NPC469790
0.7913	Intermediate Similarity	NPC472868
0.7903	Intermediate Similarity	NPC153700
0.7903	Intermediate Similarity	NPC88326
0.7903	Intermediate Similarity	NPC470265
0.7903	Intermediate Similarity	NPC23786
0.7899	Intermediate Similarity	NPC191620
0.7899	Intermediate Similarity	NPC100267
0.7899	Intermediate Similarity	NPC475524
0.7895	Intermediate Similarity	NPC114540

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 NPC184555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	876
0.2-0.3	1610
0.3-0.4	2574
0.4-0.5	2252
0.5-0.6	1089
0.6-0.7	376
0.7-0.8	62
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.824	Intermediate Similarity	NPD7319	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7946	Intermediate Similarity	NPD7638	Approved
0.7934	Intermediate Similarity	NPD7115	Discovery
0.7876	Intermediate Similarity	NPD7640	Approved
0.7876	Intermediate Similarity	NPD7639	Approved
0.7863	Intermediate Similarity	NPD6899	Approved
0.7863	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7731	Intermediate Similarity	NPD7102	Approved
0.7731	Intermediate Similarity	NPD6883	Approved
0.7731	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.768	Intermediate Similarity	NPD7503	Approved
0.7667	Intermediate Similarity	NPD6847	Approved
0.7667	Intermediate Similarity	NPD6649	Approved
0.7667	Intermediate Similarity	NPD6617	Approved
0.7667	Intermediate Similarity	NPD8130	Phase 1
0.7667	Intermediate Similarity	NPD6650	Approved
0.7667	Intermediate Similarity	NPD6869	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.7603	Intermediate Similarity	NPD6053	Discontinued
0.7603	Intermediate Similarity	NPD6882	Approved
0.7603	Intermediate Similarity	NPD8297	Approved
0.76	Intermediate Similarity	NPD6319	Approved
0.7597	Intermediate Similarity	NPD7736	Approved
0.7586	Intermediate Similarity	NPD5211	Phase 2
0.7583	Intermediate Similarity	NPD4634	Approved
0.7565	Intermediate Similarity	NPD5285	Approved
0.7565	Intermediate Similarity	NPD5286	Approved
0.7565	Intermediate Similarity	NPD4696	Approved
0.7563	Intermediate Similarity	NPD7320	Approved
0.7563	Intermediate Similarity	NPD6011	Approved
0.7541	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.7479	Intermediate Similarity	NPD5701	Approved
0.746	Intermediate Similarity	NPD6054	Approved
0.7458	Intermediate Similarity	NPD5141	Approved
0.7442	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD5224	Approved
0.7436	Intermediate Similarity	NPD5226	Approved
0.7436	Intermediate Similarity	NPD4633	Approved
0.7436	Intermediate Similarity	NPD5225	Approved
0.7411	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7385	Intermediate Similarity	NPD7078	Approved
0.7373	Intermediate Similarity	NPD5175	Approved
0.7373	Intermediate Similarity	NPD5174	Approved
0.736	Intermediate Similarity	NPD6009	Approved
0.735	Intermediate Similarity	NPD5223	Approved
0.7344	Intermediate Similarity	NPD6370	Approved
0.7302	Intermediate Similarity	NPD7327	Approved
0.7302	Intermediate Similarity	NPD7328	Approved
0.7288	Intermediate Similarity	NPD7632	Discontinued
0.7266	Intermediate Similarity	NPD6015	Approved
0.7266	Intermediate Similarity	NPD6016	Approved
0.7265	Intermediate Similarity	NPD4700	Approved
0.7257	Intermediate Similarity	NPD7637	Suspended
0.7244	Intermediate Similarity	NPD7100	Approved
0.7244	Intermediate Similarity	NPD7516	Approved
0.7244	Intermediate Similarity	NPD7101	Approved
0.7241	Intermediate Similarity	NPD6084	Phase 2
0.7241	Intermediate Similarity	NPD6083	Phase 2
0.7236	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5328	Approved
0.7209	Intermediate Similarity	NPD5988	Approved
0.7188	Intermediate Similarity	NPD6059	Approved
0.7165	Intermediate Similarity	NPD6335	Approved
0.7155	Intermediate Similarity	NPD5221	Approved
0.7155	Intermediate Similarity	NPD5222	Approved
0.7155	Intermediate Similarity	NPD4697	Phase 3
0.7155	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD6274	Approved
0.7132	Intermediate Similarity	NPD8379	Approved
0.7132	Intermediate Similarity	NPD5983	Phase 2
0.7132	Intermediate Similarity	NPD8296	Approved
0.7132	Intermediate Similarity	NPD8378	Approved
0.7132	Intermediate Similarity	NPD8380	Approved
0.7132	Intermediate Similarity	NPD8335	Approved
0.7131	Intermediate Similarity	NPD4729	Approved
0.7131	Intermediate Similarity	NPD4730	Approved
0.7121	Intermediate Similarity	NPD8293	Discontinued
0.7107	Intermediate Similarity	NPD6008	Approved
0.7105	Intermediate Similarity	NPD7515	Phase 2
0.7094	Intermediate Similarity	NPD5173	Approved
0.7087	Intermediate Similarity	NPD6317	Approved
0.7054	Intermediate Similarity	NPD8294	Approved
0.7054	Intermediate Similarity	NPD8377	Approved
0.7045	Intermediate Similarity	NPD6336	Discontinued
0.7043	Intermediate Similarity	NPD5778	Approved
0.7043	Intermediate Similarity	NPD5779	Approved
0.7043	Intermediate Similarity	NPD4202	Approved
0.7034	Intermediate Similarity	NPD4225	Approved
0.7031	Intermediate Similarity	NPD6313	Approved
0.7031	Intermediate Similarity	NPD6314	Approved
0.7027	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5785	Approved
0.7016	Intermediate Similarity	NPD5249	Phase 3
0.7016	Intermediate Similarity	NPD5250	Approved
0.7016	Intermediate Similarity	NPD5247	Approved
0.7016	Intermediate Similarity	NPD5251	Approved
0.7016	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD8033	Approved
0.6992	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5128	Approved
0.6991	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7748	Approved
0.6967	Remote Similarity	NPD4767	Approved
0.6967	Remote Similarity	NPD4768	Approved
0.696	Remote Similarity	NPD5216	Approved
0.696	Remote Similarity	NPD5217	Approved
0.696	Remote Similarity	NPD5215	Approved
0.6957	Remote Similarity	NPD5281	Approved
0.6957	Remote Similarity	NPD6411	Approved
0.6957	Remote Similarity	NPD5284	Approved
0.6942	Remote Similarity	NPD4754	Approved
0.6935	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6891	Remote Similarity	NPD5696	Approved
0.688	Remote Similarity	NPD5135	Approved
0.688	Remote Similarity	NPD5169	Approved
0.688	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6868	Approved
0.687	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6908	Approved
0.687	Remote Similarity	NPD6909	Approved
0.6855	Remote Similarity	NPD6686	Approved
0.6849	Remote Similarity	NPD7236	Approved
0.6847	Remote Similarity	NPD4788	Approved
0.6825	Remote Similarity	NPD5127	Approved
0.6814	Remote Similarity	NPD6409	Approved
0.6814	Remote Similarity	NPD3618	Phase 1
0.6814	Remote Similarity	NPD7521	Approved
0.6814	Remote Similarity	NPD5330	Approved
0.6814	Remote Similarity	NPD7146	Approved
0.6814	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6684	Approved
0.6814	Remote Similarity	NPD7334	Approved
0.681	Remote Similarity	NPD8034	Phase 2
0.681	Remote Similarity	NPD8035	Phase 2
0.681	Remote Similarity	NPD5693	Phase 1
0.6807	Remote Similarity	NPD7902	Approved
0.6786	Remote Similarity	NPD3666	Approved
0.6786	Remote Similarity	NPD3133	Approved
0.6786	Remote Similarity	NPD3665	Phase 1
0.6783	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6101	Approved
0.678	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD3573	Approved
0.6752	Remote Similarity	NPD6399	Phase 3
0.6746	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8513	Phase 3
0.6732	Remote Similarity	NPD5761	Phase 2
0.6732	Remote Similarity	NPD5760	Phase 2
0.6719	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD6903	Approved
0.6691	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6642	Remote Similarity	NPD8328	Phase 3
0.6638	Remote Similarity	NPD6051	Approved
0.6638	Remote Similarity	NPD6080	Approved
0.6638	Remote Similarity	NPD6904	Approved
0.6638	Remote Similarity	NPD6673	Approved
0.6637	Remote Similarity	NPD4786	Approved
0.6623	Remote Similarity	NPD7239	Suspended
0.6617	Remote Similarity	NPD8515	Approved
0.6617	Remote Similarity	NPD8516	Approved
0.6617	Remote Similarity	NPD8517	Approved
0.6614	Remote Similarity	NPD6371	Approved
0.6607	Remote Similarity	NPD4223	Phase 3
0.6607	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4221	Approved
0.6587	Remote Similarity	NPD5168	Approved
0.6581	Remote Similarity	NPD5207	Approved
0.6581	Remote Similarity	NPD5692	Phase 3
0.6579	Remote Similarity	NPD5329	Approved
0.6579	Remote Similarity	NPD5363	Approved
0.6577	Remote Similarity	NPD7525	Registered
0.6555	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7900	Approved
0.6552	Remote Similarity	NPD5737	Approved
0.6552	Remote Similarity	NPD6672	Approved
0.6549	Remote Similarity	NPD6695	Phase 3
0.6547	Remote Similarity	NPD7260	Phase 2
0.6545	Remote Similarity	NPD6697	Approved
0.6545	Remote Similarity	NPD6115	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