NPASS Compound

Structure

CID328371 OpenBabel06191716202D 35 38 0 0 1 0 0 0 0 0999 V2000 -0.0044 2.9295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2309 3.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6955 4.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 2.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8407 3.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6950 2.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5404 3.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2300 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2298 0.4873 0.0000 C 0 0 0 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 0.8454 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -1.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 1.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8498 3.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3855 2.9285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8501 4.3933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8460 -1.4653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3852 1.9525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5386 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6914 -0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6920 -0.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8466 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6923 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 4.8815 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 -2.5389 1.4642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5577 -1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5579 -1.4778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0193 1.9650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0053 5.8576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 4.3938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 3 18 1 0 0 0 0 7 35 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 17 2 1 6 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 30 1 6 0 0 0 22 29 1 6 0 0 0 23 31 2 0 0 0 0 24 26 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 26 27 2 0 0 0 0 27 29 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	523.979
LogP:	4.647
LogD:	5.025
LogS:	-4.88
# Rotatable Bonds:	6
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	5.021
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.896
MDCK Permeability:	1.9805413103313185e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.89
Plasma Protein Binding (PPB):	91.73198699951172%
Volume Distribution (VD):	0.746
Pgp-substrate:	2.6228296756744385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.383
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.764

ADMET: Excretion

Clearance (CL):	15.384
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.336
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.031
Carcinogencity:	0.027
Eye Corrosion:	0.017
Eye Irritation:	0.016
Respiratory Toxicity:	0.126

Download Data

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

Natural Product: NPC328371

Natural Product ID:	NPC328371
*Common Name:**	Camphoratin F
IUPAC Name:	methyl (6R)-6-[(4S,5S,7S,10S,13R,14R,17R)-7-hydroxy-4,10,13-trimethyl-3,11-dioxo-2,4,5,6,7,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoate
Synonyms:	Camphoratin F
Standard InCHIKey:	KREJDSDDOCJSGN-VFJZLOOJSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-16(18(3)28(34)35-7)8-9-17(2)20-10-11-21-26-24(32)14-22-19(4)23(31)12-13-29(22,5)27(26)25(33)15-30(20,21)6/h17-22,24,32H,1,8-15H2,2-7H3/t17-,18?,19+,20-,21+,22+,24+,29+,30-/m1/s1
SMILES:	COC(=O)C(C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CCC(=O)[C@H]2C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641969
PubChem CID:	50900841
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:0000260] Monohydroxy 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
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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]
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]
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
ED50	4
IC50	4

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	2500.0	nM	PMID[476699]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[476699]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	=	4.4	ug ml-1	PMID[476699]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	7.9	ug ml-1	PMID[476699]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	8.9	ug ml-1	PMID[476699]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	2000.0	nM	PMID[476700]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2500.0	nM	PMID[476700]
NPT2	Others	Unspecified		IC50	=	11200.0	nM	PMID[476699]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2900.0	nM	PMID[476700]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11200.0	nM	PMID[476700]

☑ 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 NPC328371 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	165
0.1-0.2	1026
0.2-0.3	4431
0.3-0.4	10862
0.4-0.5	11139
0.5-0.6	6624
0.6-0.7	5799
0.7-0.8	2227
0.8-0.85	266
0.85-0.9	91
0.9-0.95	59
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC174948
0.9888	High Similarity	NPC318282
0.9888	High Similarity	NPC469995
0.9888	High Similarity	NPC173875
0.9556	High Similarity	NPC184870
0.9468	High Similarity	NPC308726
0.9468	High Similarity	NPC119601
0.9457	High Similarity	NPC18319
0.9451	High Similarity	NPC470016
0.9451	High Similarity	NPC317586
0.9438	High Similarity	NPC477147
0.9438	High Similarity	NPC477149
0.9368	High Similarity	NPC236390
0.9362	High Similarity	NPC163372
0.9362	High Similarity	NPC302537
0.9355	High Similarity	NPC471717
0.9355	High Similarity	NPC197386
0.9348	High Similarity	NPC3772
0.9341	High Similarity	NPC166906
0.9326	High Similarity	NPC214387
0.9263	High Similarity	NPC204450
0.9263	High Similarity	NPC195290
0.9255	High Similarity	NPC287833
0.9255	High Similarity	NPC205899
0.9255	High Similarity	NPC51370
0.9247	High Similarity	NPC106557
0.9247	High Similarity	NPC121339
0.9247	High Similarity	NPC320306
0.9239	High Similarity	NPC37646
0.9231	High Similarity	NPC470254
0.9231	High Similarity	NPC472930
0.9158	High Similarity	NPC472924
0.9149	High Similarity	NPC10364
0.914	High Similarity	NPC243525
0.914	High Similarity	NPC96859
0.914	High Similarity	NPC472941
0.914	High Similarity	NPC328162
0.914	High Similarity	NPC40765
0.914	High Similarity	NPC456
0.914	High Similarity	NPC305483
0.9121	High Similarity	NPC107690
0.9121	High Similarity	NPC63748
0.9062	High Similarity	NPC56498
0.9053	High Similarity	NPC327431
0.9032	High Similarity	NPC472932
0.9022	High Similarity	NPC69454
0.898	High Similarity	NPC323834
0.8947	High Similarity	NPC166745
0.8947	High Similarity	NPC235464
0.8936	High Similarity	NPC7124
0.8936	High Similarity	NPC249954
0.8889	High Similarity	NPC472925
0.8878	High Similarity	NPC28656
0.8866	High Similarity	NPC136289
0.8854	High Similarity	NPC476274
0.8854	High Similarity	NPC316964
0.8842	High Similarity	NPC43747
0.883	High Similarity	NPC259286
0.8817	High Similarity	NPC25750
0.8817	High Similarity	NPC206810
0.8804	High Similarity	NPC48010
0.8804	High Similarity	NPC469400
0.88	High Similarity	NPC295244
0.8791	High Similarity	NPC131470
0.8791	High Similarity	NPC242864
0.8791	High Similarity	NPC143767
0.8778	High Similarity	NPC322159
0.8776	High Similarity	NPC251017
0.8776	High Similarity	NPC55872
0.8763	High Similarity	NPC224720
0.8763	High Similarity	NPC476240
0.8763	High Similarity	NPC476223
0.8763	High Similarity	NPC99411
0.8763	High Similarity	NPC81530
0.8737	High Similarity	NPC125622
0.8737	High Similarity	NPC95565
0.8723	High Similarity	NPC469406
0.871	High Similarity	NPC233116
0.8696	High Similarity	NPC86319
0.8696	High Similarity	NPC275740
0.8696	High Similarity	NPC123912
0.8673	High Similarity	NPC473424
0.8673	High Similarity	NPC293753
0.8673	High Similarity	NPC234892
0.8667	High Similarity	NPC474083
0.866	High Similarity	NPC88198
0.866	High Similarity	NPC307954
0.866	High Similarity	NPC144660
0.866	High Similarity	NPC299971
0.8652	High Similarity	NPC470015
0.8652	High Similarity	NPC168188
0.8646	High Similarity	NPC253826
0.8646	High Similarity	NPC122294
0.8632	High Similarity	NPC255809
0.8632	High Similarity	NPC241156
0.8632	High Similarity	NPC48330
0.8632	High Similarity	NPC476174
0.8627	High Similarity	NPC37116
0.8617	High Similarity	NPC243866
0.8602	High Similarity	NPC183283
0.86	High Similarity	NPC51452
0.8587	High Similarity	NPC471722
0.8571	High Similarity	NPC55309
0.8571	High Similarity	NPC72133
0.8571	High Similarity	NPC28252
0.8558	High Similarity	NPC472926
0.8557	High Similarity	NPC16021
0.8557	High Similarity	NPC478056
0.8557	High Similarity	NPC114274
0.8556	High Similarity	NPC473246
0.8556	High Similarity	NPC165064
0.8544	High Similarity	NPC472928
0.8542	High Similarity	NPC173272
0.8542	High Similarity	NPC42042
0.8539	High Similarity	NPC321289
0.8539	High Similarity	NPC327969
0.8529	High Similarity	NPC286174
0.8529	High Similarity	NPC77947
0.8515	High Similarity	NPC473037
0.8515	High Similarity	NPC475294
0.8515	High Similarity	NPC91034
0.8511	High Similarity	NPC473998
0.8511	High Similarity	NPC26888
0.8511	High Similarity	NPC297265
0.8495	Intermediate Similarity	NPC31985
0.8495	Intermediate Similarity	NPC474889
0.8495	Intermediate Similarity	NPC54689
0.8495	Intermediate Similarity	NPC473999
0.8495	Intermediate Similarity	NPC146554
0.8495	Intermediate Similarity	NPC1015
0.8495	Intermediate Similarity	NPC309603
0.8485	Intermediate Similarity	NPC281702
0.8478	Intermediate Similarity	NPC136948
0.8478	Intermediate Similarity	NPC159046
0.8478	Intermediate Similarity	NPC233836
0.8478	Intermediate Similarity	NPC475740
0.8478	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC477521
0.8469	Intermediate Similarity	NPC241221
0.8469	Intermediate Similarity	NPC266955
0.8469	Intermediate Similarity	NPC157787
0.8469	Intermediate Similarity	NPC218383
0.8462	Intermediate Similarity	NPC469948
0.8462	Intermediate Similarity	NPC94531
0.8462	Intermediate Similarity	NPC311702
0.8462	Intermediate Similarity	NPC471224
0.8462	Intermediate Similarity	NPC123319
0.8454	Intermediate Similarity	NPC107243
0.8454	Intermediate Similarity	NPC141401
0.8454	Intermediate Similarity	NPC108078
0.8454	Intermediate Similarity	NPC475894
0.8447	Intermediate Similarity	NPC272898
0.8447	Intermediate Similarity	NPC129689
0.8447	Intermediate Similarity	NPC473036
0.8438	Intermediate Similarity	NPC469599
0.8421	Intermediate Similarity	NPC214697
0.8421	Intermediate Similarity	NPC472942
0.8421	Intermediate Similarity	NPC474736
0.8404	Intermediate Similarity	NPC289213
0.8404	Intermediate Similarity	NPC69622
0.8404	Intermediate Similarity	NPC175628
0.8404	Intermediate Similarity	NPC111585
0.8404	Intermediate Similarity	NPC148414
0.8404	Intermediate Similarity	NPC20388
0.84	Intermediate Similarity	NPC111323
0.84	Intermediate Similarity	NPC33973
0.84	Intermediate Similarity	NPC70967
0.8387	Intermediate Similarity	NPC328539
0.8384	Intermediate Similarity	NPC115899
0.8381	Intermediate Similarity	NPC472929
0.837	Intermediate Similarity	NPC145879
0.837	Intermediate Similarity	NPC222613
0.837	Intermediate Similarity	NPC474778
0.837	Intermediate Similarity	NPC474732
0.837	Intermediate Similarity	NPC475022
0.837	Intermediate Similarity	NPC118648
0.837	Intermediate Similarity	NPC474733
0.837	Intermediate Similarity	NPC31564
0.837	Intermediate Similarity	NPC155011
0.8367	Intermediate Similarity	NPC48647
0.8365	Intermediate Similarity	NPC115303
0.8352	Intermediate Similarity	NPC85774
0.8352	Intermediate Similarity	NPC164577
0.8352	Intermediate Similarity	NPC320801
0.8352	Intermediate Similarity	NPC214043
0.8351	Intermediate Similarity	NPC471463
0.8351	Intermediate Similarity	NPC29152
0.8351	Intermediate Similarity	NPC155676
0.8351	Intermediate Similarity	NPC117133
0.8351	Intermediate Similarity	NPC120708
0.8351	Intermediate Similarity	NPC250757
0.8351	Intermediate Similarity	NPC301534
0.8333	Intermediate Similarity	NPC8993
0.8333	Intermediate Similarity	NPC260956
0.8318	Intermediate Similarity	NPC472927
0.8317	Intermediate Similarity	NPC2436
0.8317	Intermediate Similarity	NPC235889
0.8317	Intermediate Similarity	NPC135854
0.8317	Intermediate Similarity	NPC216245
0.8317	Intermediate Similarity	NPC470251

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 NPC328371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1378
0.2-0.3	3768
0.3-0.4	2572
0.4-0.5	757
0.5-0.6	203
0.6-0.7	181
0.7-0.8	145
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD5328	Approved
0.8316	Intermediate Similarity	NPD6079	Approved
0.8235	Intermediate Similarity	NPD7128	Approved
0.8235	Intermediate Similarity	NPD5739	Approved
0.8235	Intermediate Similarity	NPD6675	Approved
0.8235	Intermediate Similarity	NPD6402	Approved
0.8229	Intermediate Similarity	NPD6399	Phase 3
0.8152	Intermediate Similarity	NPD4786	Approved
0.8081	Intermediate Similarity	NPD6083	Phase 2
0.8081	Intermediate Similarity	NPD6084	Phase 2
0.8077	Intermediate Similarity	NPD7320	Approved
0.8077	Intermediate Similarity	NPD6899	Approved
0.8077	Intermediate Similarity	NPD6881	Approved
0.8061	Intermediate Similarity	NPD5695	Phase 3
0.8	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD6672	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.7981	Intermediate Similarity	NPD5697	Approved
0.7981	Intermediate Similarity	NPD5701	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD4697	Phase 3
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD7146	Approved
0.7979	Intermediate Similarity	NPD7521	Approved
0.7979	Intermediate Similarity	NPD7334	Approved
0.7979	Intermediate Similarity	NPD6409	Approved
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7979	Intermediate Similarity	NPD5279	Phase 3
0.7979	Intermediate Similarity	NPD6684	Approved
0.7979	Intermediate Similarity	NPD5330	Approved
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7935	Intermediate Similarity	NPD3667	Approved
0.7925	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD7290	Approved
0.7925	Intermediate Similarity	NPD7102	Approved
0.7921	Intermediate Similarity	NPD7640	Approved
0.7921	Intermediate Similarity	NPD7639	Approved
0.7905	Intermediate Similarity	NPD6011	Approved
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD4755	Approved
0.785	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD6617	Approved
0.785	Intermediate Similarity	NPD6649	Approved
0.785	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD6869	Approved
0.785	Intermediate Similarity	NPD8130	Phase 1
0.785	Intermediate Similarity	NPD6847	Approved
0.783	Intermediate Similarity	NPD6013	Approved
0.783	Intermediate Similarity	NPD6012	Approved
0.783	Intermediate Similarity	NPD6014	Approved
0.7822	Intermediate Similarity	NPD7638	Approved
0.7818	Intermediate Similarity	NPD7115	Discovery
0.7812	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6903	Approved
0.7788	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7745	Intermediate Similarity	NPD5286	Approved
0.7745	Intermediate Similarity	NPD4700	Approved
0.7745	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD4753	Phase 2
0.7692	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4202	Approved
0.767	Intermediate Similarity	NPD5223	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7596	Intermediate Similarity	NPD5224	Approved
0.7596	Intermediate Similarity	NPD5225	Approved
0.7596	Intermediate Similarity	NPD5226	Approved
0.7596	Intermediate Similarity	NPD4633	Approved
0.7576	Intermediate Similarity	NPD6411	Approved
0.7576	Intermediate Similarity	NPD6050	Approved
0.7568	Intermediate Similarity	NPD6868	Approved
0.7553	Intermediate Similarity	NPD4223	Phase 3
0.7553	Intermediate Similarity	NPD4221	Approved
0.7551	Intermediate Similarity	NPD6904	Approved
0.7551	Intermediate Similarity	NPD6673	Approved
0.7551	Intermediate Similarity	NPD6080	Approved
0.7549	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD6008	Approved
0.7545	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5175	Approved
0.7524	Intermediate Similarity	NPD4754	Approved
0.7524	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7475	Intermediate Similarity	NPD5785	Approved
0.7475	Intermediate Similarity	NPD5692	Phase 3
0.7474	Intermediate Similarity	NPD5362	Discontinued
0.7455	Intermediate Similarity	NPD6053	Discontinued
0.7434	Intermediate Similarity	NPD6335	Approved
0.7429	Intermediate Similarity	NPD7632	Discontinued
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD5786	Approved
0.7423	Intermediate Similarity	NPD5280	Approved
0.7423	Intermediate Similarity	NPD4694	Approved
0.7411	Intermediate Similarity	NPD6274	Approved
0.7404	Intermediate Similarity	NPD6404	Discontinued
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD5694	Approved
0.74	Intermediate Similarity	NPD8034	Phase 2
0.74	Intermediate Similarity	NPD5693	Phase 1
0.7396	Intermediate Similarity	NPD4197	Approved
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7383	Intermediate Similarity	NPD4767	Approved
0.7383	Intermediate Similarity	NPD4768	Approved
0.7374	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6101	Approved
0.7368	Intermediate Similarity	NPD7100	Approved
0.7368	Intermediate Similarity	NPD7101	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.7345	Intermediate Similarity	NPD6317	Approved
0.7345	Intermediate Similarity	NPD6009	Approved
0.732	Intermediate Similarity	NPD5363	Approved
0.7312	Intermediate Similarity	NPD3617	Approved
0.73	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7281	Intermediate Similarity	NPD6314	Approved
0.7281	Intermediate Similarity	NPD6313	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.7248	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD4729	Approved
0.7248	Intermediate Similarity	NPD5168	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD4519	Discontinued
0.7245	Intermediate Similarity	NPD4138	Approved
0.7245	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD4693	Phase 3
0.7245	Intermediate Similarity	NPD5205	Approved
0.7245	Intermediate Similarity	NPD4689	Approved
0.7245	Intermediate Similarity	NPD4688	Approved
0.7245	Intermediate Similarity	NPD4623	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6909	Approved
0.7241	Intermediate Similarity	NPD6908	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4270	Approved
0.7188	Intermediate Similarity	NPD4269	Approved
0.7174	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD6942	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.7158	Intermediate Similarity	NPD4695	Discontinued
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7117	Intermediate Similarity	NPD5169	Approved
0.7117	Intermediate Similarity	NPD5249	Phase 3
0.7117	Intermediate Similarity	NPD5250	Approved
0.7117	Intermediate Similarity	NPD5251	Approved
0.7117	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5247	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7117	Intermediate Similarity	NPD5248	Approved
0.7117	Intermediate Similarity	NPD5135	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7083	Intermediate Similarity	NPD4139	Approved
0.7065	Intermediate Similarity	NPD5733	Approved
0.7059	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD5217	Approved
0.7054	Intermediate Similarity	NPD5127	Approved
0.7054	Intermediate Similarity	NPD5216	Approved
0.7054	Intermediate Similarity	NPD5215	Approved
0.703	Intermediate Similarity	NPD6051	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7019	Intermediate Similarity	NPD5654	Approved
0.701	Intermediate Similarity	NPD6435	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD6336	Discontinued
0.6979	Remote Similarity	NPD5368	Approved
0.6979	Remote Similarity	NPD4252	Approved
0.6979	Remote Similarity	NPD7525	Registered
0.6961	Remote Similarity	NPD4096	Approved
0.6952	Remote Similarity	NPD7614	Phase 1

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