NPASS Compound

Structure

CID316964 OpenBabel06191716132D 35 38 0 0 1 0 0 0 0 0999 V2000 -0.0044 2.9274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2279 3.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 4.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5374 2.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -2.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 2.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5386 3.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2271 1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2268 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8492 3.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 2.9265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8495 4.3902 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3828 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5368 0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6909 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6902 -0.9759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6911 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 4.8781 0.0000 C 0 0 0 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 -2.5371 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5567 -1.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0199 1.9639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5565 -1.4755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0053 5.8534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 4.3907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7114 -1.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 3 17 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 6 0 0 0 19 24 1 0 0 0 0 19 28 1 6 0 0 0 20 24 1 0 0 0 0 20 30 2 0 0 0 0 21 25 1 0 0 0 0 21 31 2 0 0 0 0 22 27 1 6 0 0 0 22 29 1 0 0 0 0 23 29 1 1 0 0 0 23 32 1 0 0 0 0 24 25 2 0 0 0 0 25 27 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	515.473
LogP:	3.432
LogD:	1.747
LogS:	-4.025
# Rotatable Bonds:	5
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	5.563
Fsp3:	0.759
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097
MDCK Permeability:	2.2059928596718237e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.92
Human Intestinal Absorption (HIA):	0.469
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	94.6806640625%
Volume Distribution (VD):	0.601
Pgp-substrate:	5.141610145568848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.341
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	7.085
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.369
Skin Sensitization:	0.079
Carcinogencity:	0.052
Eye Corrosion:	0.005
Eye Irritation:	0.01
Respiratory Toxicity:	0.79

Download Data

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

Natural Product: NPC316964

Natural Product ID:	NPC316964
*Common Name:**	Camphoratin C
IUPAC Name:	(6R)-6-[(3R,4R,5R,10S,13R,14R,17R)-3,4-dihydroxy-4,10,13-trimethyl-7,11-dioxo-1,2,3,5,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:	Camphoratin C
Standard InCHIKey:	VQOGQXBQGQLQDY-JUVRMLKSSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-15(17(3)26(33)34)7-8-16(2)18-9-10-19-24-20(30)13-22-27(4,12-11-23(32)29(22,6)35)25(24)21(31)14-28(18,19)5/h16-19,22-23,32,35H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18-,19+,22-,23-,27+,28-,29-/m1/s1
SMILES:	CC(CCC(=C)C(C)C(=O)O)C1CCC2C1(CC(=O)C3=C2C(=O)CC4C3(CCC(C4(C)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641966
PubChem CID:	50900755
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 [CHEMONTID:0000516] Dihydroxy 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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	300.0	nM	PMID[502846]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	48800.0	nM	PMID[502847]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	62800.0	nM	PMID[502847]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2300.0	nM	PMID[502846]

☑ 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 NPC316964 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	188
0.1-0.2	1237
0.2-0.3	4795
0.3-0.4	11115
0.4-0.5	10652
0.5-0.6	6263
0.6-0.7	5968
0.7-0.8	2121
0.8-0.85	267
0.85-0.9	73
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC166906
0.9355	High Similarity	NPC470016
0.9355	High Similarity	NPC317586
0.9286	High Similarity	NPC323834
0.9255	High Similarity	NPC328162
0.9255	High Similarity	NPC305483
0.9255	High Similarity	NPC96859
0.9149	High Similarity	NPC200702
0.9053	High Similarity	NPC95565
0.8958	High Similarity	NPC43747
0.8947	High Similarity	NPC318282
0.8947	High Similarity	NPC255809
0.8947	High Similarity	NPC173875
0.8947	High Similarity	NPC174948
0.8947	High Similarity	NPC469995
0.8913	High Similarity	NPC131470
0.8913	High Similarity	NPC242864
0.8913	High Similarity	NPC143767
0.8878	High Similarity	NPC163372
0.8878	High Similarity	NPC302537
0.8854	High Similarity	NPC328371
0.883	High Similarity	NPC189520
0.8817	High Similarity	NPC275740
0.8817	High Similarity	NPC86319
0.8804	High Similarity	NPC138756
0.8788	High Similarity	NPC119601
0.8788	High Similarity	NPC308726
0.8788	High Similarity	NPC473424
0.8788	High Similarity	NPC477915
0.8776	High Similarity	NPC88198
0.8776	High Similarity	NPC157787
0.8763	High Similarity	NPC320306
0.875	High Similarity	NPC473170
0.875	High Similarity	NPC48330
0.8737	High Similarity	NPC25750
0.8723	High Similarity	NPC469400
0.8723	High Similarity	NPC183283
0.8723	High Similarity	NPC136801
0.8723	High Similarity	NPC289213
0.8713	High Similarity	NPC149047
0.871	High Similarity	NPC471722
0.87	High Similarity	NPC264048
0.8696	High Similarity	NPC28252
0.8696	High Similarity	NPC72133
0.8696	High Similarity	NPC55309
0.8673	High Similarity	NPC114274
0.866	High Similarity	NPC173272
0.866	High Similarity	NPC249954
0.8632	High Similarity	NPC23434
0.8632	High Similarity	NPC155304
0.8632	High Similarity	NPC297265
0.8632	High Similarity	NPC63748
0.8627	High Similarity	NPC475060
0.8627	High Similarity	NPC220229
0.8617	High Similarity	NPC32830
0.8614	High Similarity	NPC204833
0.8614	High Similarity	NPC209502
0.8614	High Similarity	NPC477812
0.8602	High Similarity	NPC187376
0.8602	High Similarity	NPC159046
0.8602	High Similarity	NPC233836
0.86	High Similarity	NPC195290
0.86	High Similarity	NPC204450
0.8586	High Similarity	NPC287833
0.8586	High Similarity	NPC327431
0.8586	High Similarity	NPC51370
0.8571	High Similarity	NPC108078
0.8558	High Similarity	NPC239097
0.8557	High Similarity	NPC37646
0.8557	High Similarity	NPC259286
0.8557	High Similarity	NPC241156
0.8544	High Similarity	NPC295244
0.8544	High Similarity	NPC217201
0.8542	High Similarity	NPC206810
0.8542	High Similarity	NPC69454
0.8529	High Similarity	NPC214264
0.8529	High Similarity	NPC171137
0.8529	High Similarity	NPC152695
0.8529	High Similarity	NPC260268
0.8529	High Similarity	NPC85829
0.8529	High Similarity	NPC48733
0.8529	High Similarity	NPC319077
0.8529	High Similarity	NPC476027
0.8529	High Similarity	NPC97202
0.8529	High Similarity	NPC50692
0.8529	High Similarity	NPC49958
0.8529	High Similarity	NPC296945
0.8529	High Similarity	NPC302607
0.8529	High Similarity	NPC202167
0.8529	High Similarity	NPC150531
0.8515	High Similarity	NPC236390
0.8515	High Similarity	NPC55872
0.8515	High Similarity	NPC191892
0.8515	High Similarity	NPC251017
0.8515	High Similarity	NPC70967
0.8515	High Similarity	NPC33973
0.8511	High Similarity	NPC328539
0.8491	Intermediate Similarity	NPC250109
0.8491	Intermediate Similarity	NPC962
0.8485	Intermediate Similarity	NPC10364
0.8485	Intermediate Similarity	NPC471717
0.8485	Intermediate Similarity	NPC197386
0.8469	Intermediate Similarity	NPC117133
0.8469	Intermediate Similarity	NPC40765
0.8469	Intermediate Similarity	NPC104568
0.8469	Intermediate Similarity	NPC3772
0.8469	Intermediate Similarity	NPC243525
0.8469	Intermediate Similarity	NPC125622
0.8462	Intermediate Similarity	NPC11710
0.8462	Intermediate Similarity	NPC214644
0.8454	Intermediate Similarity	NPC184870
0.8447	Intermediate Similarity	NPC472925
0.8447	Intermediate Similarity	NPC83744
0.8447	Intermediate Similarity	NPC477916
0.8438	Intermediate Similarity	NPC168027
0.8438	Intermediate Similarity	NPC107690
0.8438	Intermediate Similarity	NPC19114
0.8438	Intermediate Similarity	NPC212301
0.8438	Intermediate Similarity	NPC26888
0.8438	Intermediate Similarity	NPC86266
0.8438	Intermediate Similarity	NPC110657
0.8438	Intermediate Similarity	NPC185936
0.8431	Intermediate Similarity	NPC470251
0.8431	Intermediate Similarity	NPC96268
0.8431	Intermediate Similarity	NPC28656
0.8431	Intermediate Similarity	NPC471293
0.8431	Intermediate Similarity	NPC216245
0.8431	Intermediate Similarity	NPC135854
0.8431	Intermediate Similarity	NPC2436
0.8426	Intermediate Similarity	NPC470959
0.8426	Intermediate Similarity	NPC471854
0.8426	Intermediate Similarity	NPC476965
0.8421	Intermediate Similarity	NPC474889
0.8421	Intermediate Similarity	NPC77263
0.8421	Intermediate Similarity	NPC214387
0.8421	Intermediate Similarity	NPC1015
0.8421	Intermediate Similarity	NPC31985
0.8421	Intermediate Similarity	NPC102414
0.8421	Intermediate Similarity	NPC250592
0.8421	Intermediate Similarity	NPC54689
0.8421	Intermediate Similarity	NPC475921
0.8421	Intermediate Similarity	NPC77168
0.8421	Intermediate Similarity	NPC84271
0.8421	Intermediate Similarity	NPC474704
0.8416	Intermediate Similarity	NPC234892
0.8416	Intermediate Similarity	NPC136289
0.8416	Intermediate Similarity	NPC293753
0.8404	Intermediate Similarity	NPC475740
0.8404	Intermediate Similarity	NPC99909
0.8404	Intermediate Similarity	NPC474684
0.8404	Intermediate Similarity	NPC142361
0.84	Intermediate Similarity	NPC110149
0.84	Intermediate Similarity	NPC198880
0.84	Intermediate Similarity	NPC205899
0.84	Intermediate Similarity	NPC476274
0.8396	Intermediate Similarity	NPC280782
0.8384	Intermediate Similarity	NPC122294
0.8384	Intermediate Similarity	NPC106557
0.8384	Intermediate Similarity	NPC121339
0.8384	Intermediate Similarity	NPC18319
0.8381	Intermediate Similarity	NPC37116
0.837	Intermediate Similarity	NPC470015
0.837	Intermediate Similarity	NPC168188
0.8367	Intermediate Similarity	NPC162001
0.8367	Intermediate Similarity	NPC45324
0.8367	Intermediate Similarity	NPC53565
0.8367	Intermediate Similarity	NPC469599
0.8367	Intermediate Similarity	NPC69548
0.8367	Intermediate Similarity	NPC184848
0.8367	Intermediate Similarity	NPC222845
0.8365	Intermediate Similarity	NPC329417
0.8365	Intermediate Similarity	NPC65941
0.8351	Intermediate Similarity	NPC470375
0.8351	Intermediate Similarity	NPC107674
0.8351	Intermediate Similarity	NPC133579
0.8351	Intermediate Similarity	NPC243866
0.8351	Intermediate Similarity	NPC472930
0.8351	Intermediate Similarity	NPC474806
0.8351	Intermediate Similarity	NPC470254
0.8351	Intermediate Similarity	NPC170220
0.8351	Intermediate Similarity	NPC141497
0.8351	Intermediate Similarity	NPC470376
0.835	Intermediate Similarity	NPC51452
0.835	Intermediate Similarity	NPC475494
0.835	Intermediate Similarity	NPC102352
0.8349	Intermediate Similarity	NPC257457
0.8349	Intermediate Similarity	NPC311554
0.8333	Intermediate Similarity	NPC175628
0.8333	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC477147
0.8333	Intermediate Similarity	NPC477149
0.8333	Intermediate Similarity	NPC266728
0.8333	Intermediate Similarity	NPC111585
0.8333	Intermediate Similarity	NPC20388
0.8333	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC148414
0.8333	Intermediate Similarity	NPC159442
0.8317	Intermediate Similarity	NPC124211
0.8317	Intermediate Similarity	NPC81530
0.8317	Intermediate Similarity	NPC224720

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 NPC316964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1656
0.2-0.3	3947
0.3-0.4	2263
0.4-0.5	648
0.5-0.6	178
0.6-0.7	148
0.7-0.8	142
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8617	High Similarity	NPD5328	Approved
0.8438	Intermediate Similarity	NPD6079	Approved
0.835	Intermediate Similarity	NPD6675	Approved
0.835	Intermediate Similarity	NPD5739	Approved
0.835	Intermediate Similarity	NPD7128	Approved
0.835	Intermediate Similarity	NPD6402	Approved
0.8298	Intermediate Similarity	NPD3618	Phase 1
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.8283	Intermediate Similarity	NPD4697	Phase 3
0.82	Intermediate Similarity	NPD4755	Approved
0.819	Intermediate Similarity	NPD7320	Approved
0.819	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6881	Approved
0.8163	Intermediate Similarity	NPD6399	Phase 3
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.81	Intermediate Similarity	NPD5222	Approved
0.81	Intermediate Similarity	NPD5221	Approved
0.81	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5701	Approved
0.8095	Intermediate Similarity	NPD5697	Approved
0.8085	Intermediate Similarity	NPD4786	Approved
0.8061	Intermediate Similarity	NPD7515	Phase 2
0.8056	Intermediate Similarity	NPD8297	Approved
0.8039	Intermediate Similarity	NPD4696	Approved
0.8039	Intermediate Similarity	NPD4700	Approved
0.8039	Intermediate Similarity	NPD5286	Approved
0.8039	Intermediate Similarity	NPD5285	Approved
0.8037	Intermediate Similarity	NPD7102	Approved
0.8037	Intermediate Similarity	NPD7290	Approved
0.8037	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD5173	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.7982	Intermediate Similarity	NPD4632	Approved
0.798	Intermediate Similarity	NPD4202	Approved
0.7963	Intermediate Similarity	NPD6617	Approved
0.7963	Intermediate Similarity	NPD8130	Phase 1
0.7963	Intermediate Similarity	NPD6869	Approved
0.7963	Intermediate Similarity	NPD6847	Approved
0.7963	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5223	Approved
0.7944	Intermediate Similarity	NPD6012	Approved
0.7944	Intermediate Similarity	NPD6014	Approved
0.7944	Intermediate Similarity	NPD6013	Approved
0.7928	Intermediate Similarity	NPD7115	Discovery
0.789	Intermediate Similarity	NPD6882	Approved
0.7885	Intermediate Similarity	NPD5211	Phase 2
0.7885	Intermediate Similarity	NPD5225	Approved
0.7885	Intermediate Similarity	NPD5226	Approved
0.7885	Intermediate Similarity	NPD4633	Approved
0.7885	Intermediate Similarity	NPD5224	Approved
0.7879	Intermediate Similarity	NPD5281	Approved
0.7879	Intermediate Similarity	NPD5284	Approved
0.7872	Intermediate Similarity	NPD3667	Approved
0.7843	Intermediate Similarity	NPD6083	Phase 2
0.7843	Intermediate Similarity	NPD6084	Phase 2
0.783	Intermediate Similarity	NPD6008	Approved
0.7822	Intermediate Similarity	NPD5695	Phase 3
0.7812	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5175	Approved
0.781	Intermediate Similarity	NPD4754	Approved
0.781	Intermediate Similarity	NPD5174	Approved
0.7736	Intermediate Similarity	NPD5141	Approved
0.7732	Intermediate Similarity	NPD5279	Phase 3
0.7723	Intermediate Similarity	NPD7748	Approved
0.7708	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD3133	Approved
0.7708	Intermediate Similarity	NPD3666	Approved
0.7706	Intermediate Similarity	NPD4634	Approved
0.7677	Intermediate Similarity	NPD4753	Phase 2
0.767	Intermediate Similarity	NPD7902	Approved
0.7664	Intermediate Similarity	NPD4767	Approved
0.7664	Intermediate Similarity	NPD4768	Approved
0.7647	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6009	Approved
0.7596	Intermediate Similarity	NPD5696	Approved
0.7576	Intermediate Similarity	NPD5737	Approved
0.7576	Intermediate Similarity	NPD6672	Approved
0.7565	Intermediate Similarity	NPD6319	Approved
0.7551	Intermediate Similarity	NPD6409	Approved
0.7551	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6684	Approved
0.7551	Intermediate Similarity	NPD7146	Approved
0.7551	Intermediate Similarity	NPD7521	Approved
0.7551	Intermediate Similarity	NPD7334	Approved
0.7551	Intermediate Similarity	NPD5330	Approved
0.7544	Intermediate Similarity	NPD6335	Approved
0.7525	Intermediate Similarity	NPD8034	Phase 2
0.7525	Intermediate Similarity	NPD8035	Phase 2
0.7523	Intermediate Similarity	NPD5128	Approved
0.7523	Intermediate Similarity	NPD4730	Approved
0.7523	Intermediate Similarity	NPD4729	Approved
0.7522	Intermediate Similarity	NPD6274	Approved
0.7522	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7478	Intermediate Similarity	NPD7100	Approved
0.7478	Intermediate Similarity	NPD7101	Approved
0.7476	Intermediate Similarity	NPD4629	Approved
0.7476	Intermediate Similarity	NPD5210	Approved
0.7456	Intermediate Similarity	NPD6317	Approved
0.7449	Intermediate Similarity	NPD5329	Approved
0.7429	Intermediate Similarity	NPD7638	Approved
0.74	Intermediate Similarity	NPD6903	Approved
0.74	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6313	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7387	Intermediate Similarity	NPD5249	Phase 3
0.7387	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5248	Approved
0.7387	Intermediate Similarity	NPD5247	Approved
0.7387	Intermediate Similarity	NPD5250	Approved
0.7387	Intermediate Similarity	NPD5135	Approved
0.7387	Intermediate Similarity	NPD5251	Approved
0.7387	Intermediate Similarity	NPD5169	Approved
0.7379	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7900	Approved
0.7374	Intermediate Similarity	NPD5280	Approved
0.7374	Intermediate Similarity	NPD4694	Approved
0.7374	Intermediate Similarity	NPD5690	Phase 2
0.7373	Intermediate Similarity	NPD7604	Phase 2
0.7364	Intermediate Similarity	NPD5168	Approved
0.7358	Intermediate Similarity	NPD7640	Approved
0.7358	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD6411	Approved
0.7353	Intermediate Similarity	NPD6050	Approved
0.735	Intermediate Similarity	NPD6908	Approved
0.735	Intermediate Similarity	NPD5983	Phase 2
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6909	Approved
0.7347	Intermediate Similarity	NPD3668	Phase 3
0.7347	Intermediate Similarity	NPD4197	Approved
0.7327	Intermediate Similarity	NPD6904	Approved
0.7327	Intermediate Similarity	NPD6673	Approved
0.7327	Intermediate Similarity	NPD6080	Approved
0.7321	Intermediate Similarity	NPD5215	Approved
0.7321	Intermediate Similarity	NPD5127	Approved
0.7321	Intermediate Similarity	NPD5216	Approved
0.7321	Intermediate Similarity	NPD5217	Approved
0.7311	Intermediate Similarity	NPD7492	Approved
0.73	Intermediate Similarity	NPD3573	Approved
0.7292	Intermediate Similarity	NPD7525	Registered
0.7265	Intermediate Similarity	NPD6054	Approved
0.7265	Intermediate Similarity	NPD6059	Approved
0.7255	Intermediate Similarity	NPD5207	Approved
0.7255	Intermediate Similarity	NPD5692	Phase 3
0.725	Intermediate Similarity	NPD6616	Approved
0.725	Intermediate Similarity	NPD6336	Discontinued
0.7245	Intermediate Similarity	NPD4788	Approved
0.7234	Intermediate Similarity	NPD6117	Approved
0.7212	Intermediate Similarity	NPD6001	Approved
0.72	Intermediate Similarity	NPD4693	Phase 3
0.72	Intermediate Similarity	NPD4690	Approved
0.72	Intermediate Similarity	NPD4689	Approved
0.72	Intermediate Similarity	NPD4688	Approved
0.72	Intermediate Similarity	NPD4138	Approved
0.72	Intermediate Similarity	NPD5205	Approved
0.719	Intermediate Similarity	NPD7078	Approved
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7184	Intermediate Similarity	NPD5694	Approved
0.7158	Intermediate Similarity	NPD6116	Phase 1
0.7157	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6370	Approved
0.7131	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5167	Approved
0.7128	Intermediate Similarity	NPD7339	Approved
0.7128	Intermediate Similarity	NPD6942	Approved
0.7117	Intermediate Similarity	NPD6412	Phase 2
0.7107	Intermediate Similarity	NPD7507	Approved
0.7103	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD6118	Approved
0.7083	Intermediate Similarity	NPD3617	Approved
0.7083	Intermediate Similarity	NPD6114	Approved
0.7083	Intermediate Similarity	NPD6697	Approved
0.7083	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD6015	Approved
0.7059	Intermediate Similarity	NPD5208	Approved
0.7059	Intermediate Similarity	NPD6016	Approved
0.7041	Intermediate Similarity	NPD4692	Approved
0.7041	Intermediate Similarity	NPD4139	Approved
0.703	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5693	Phase 1
0.7	Intermediate Similarity	NPD5988	Approved
0.6957	Remote Similarity	NPD6053	Discontinued
0.6942	Remote Similarity	NPD8328	Phase 3
0.6939	Remote Similarity	NPD4695	Discontinued
0.6939	Remote Similarity	NPD4748	Discontinued
0.6935	Remote Similarity	NPD7319	Approved
0.693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4096	Approved
0.6909	Remote Similarity	NPD7632	Discontinued
0.6907	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4518	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