NPASS Compound

Structure

NPC119601 OpenBabel07101718322D 36 39 0 0 1 0 0 0 0 0999 V2000 7.1527 1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1235 4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4180 3.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4836 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7926 3.3838 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 -0.0000 -1.0000 0.0000 C 0 0 2 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7707 3.5917 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0798 4.5428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4399 2.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 7 36 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 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 2 1 6 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 18 27 1 0 0 0 0 19 29 1 1 0 0 0 20 25 1 0 0 0 0 20 29 1 1 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 30 1 0 0 0 0 24 33 2 0 0 0 0 25 26 2 0 0 0 0 26 28 1 0 0 0 0 27 34 2 0 0 0 0 27 36 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 6 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	532.769
LogP:	4.148
LogD:	4.736
LogS:	-4.694
# Rotatable Bonds:	6
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	5.129
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:	-5.001
MDCK Permeability:	2.348396446905099e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.757
Plasma Protein Binding (PPB):	89.17943572998047%
Volume Distribution (VD):	0.709
Pgp-substrate:	3.605886936187744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.454
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	7.299
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.295
Skin Sensitization:	0.023
Carcinogencity:	0.011
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC119601

Natural Product ID:	NPC119601
*Common Name:**	Antcamphin H
IUPAC Name:	methyl (2R,6R)-6-[(4R,5R,7S,10S,13R,14R,17R)-4,7-dihydroxy-4,10,13-trimethyl-3,11-dioxo-1,2,5,6,7,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoate
Synonyms:
Standard InCHIKey:	HQWYIQDEBGBHLM-YFOTXEKSSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-16(18(3)27(34)36-7)8-9-17(2)19-10-11-20-25-21(31)14-23-28(4,13-12-24(33)30(23,6)35)26(25)22(32)15-29(19,20)5/h17-21,23,31,35H,1,8-15H2,2-7H3/t17-,18-,19-,20+,21+,23-,28+,29-,30-/m1/s1
SMILES:	COC(=O)[C@@H](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@]2(C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105002
PubChem CID:	76328319
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]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	93200.0	nM	PMID[512719]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	71500.0	nM	PMID[512719]

☑ 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 NPC119601 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	186
0.1-0.2	1168
0.2-0.3	4422
0.3-0.4	9799
0.4-0.5	11759
0.5-0.6	6669
0.6-0.7	6095
0.7-0.8	2250
0.8-0.85	236
0.85-0.9	93
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308726
0.9894	High Similarity	NPC302537
0.9894	High Similarity	NPC163372
0.9468	High Similarity	NPC328371
0.9362	High Similarity	NPC318282
0.9362	High Similarity	NPC469995
0.9362	High Similarity	NPC173875
0.9362	High Similarity	NPC174948
0.9263	High Similarity	NPC96859
0.9263	High Similarity	NPC305483
0.9263	High Similarity	NPC328162
0.9175	High Similarity	NPC327431
0.9167	High Similarity	NPC18319
0.9158	High Similarity	NPC317586
0.9158	High Similarity	NPC470016
0.91	High Similarity	NPC323834
0.9091	High Similarity	NPC236390
0.9053	High Similarity	NPC166906
0.9053	High Similarity	NPC184870
0.901	High Similarity	NPC472925
0.899	High Similarity	NPC204450
0.899	High Similarity	NPC195290
0.898	High Similarity	NPC205899
0.8969	High Similarity	NPC320306
0.8969	High Similarity	NPC43747
0.8936	High Similarity	NPC477147
0.8936	High Similarity	NPC477149
0.8932	High Similarity	NPC272898
0.8932	High Similarity	NPC473036
0.8922	High Similarity	NPC295244
0.89	High Similarity	NPC251017
0.8878	High Similarity	NPC197386
0.8878	High Similarity	NPC10364
0.8878	High Similarity	NPC471717
0.8866	High Similarity	NPC249954
0.8866	High Similarity	NPC3772
0.8842	High Similarity	NPC63748
0.883	High Similarity	NPC214387
0.8824	High Similarity	NPC475294
0.8812	High Similarity	NPC28656
0.88	High Similarity	NPC56498
0.88	High Similarity	NPC136289
0.8788	High Similarity	NPC316964
0.8788	High Similarity	NPC476274
0.8788	High Similarity	NPC287833
0.8788	High Similarity	NPC88198
0.8788	High Similarity	NPC51370
0.8776	High Similarity	NPC121339
0.8776	High Similarity	NPC106557
0.8763	High Similarity	NPC259286
0.8763	High Similarity	NPC37646
0.875	High Similarity	NPC69454
0.875	High Similarity	NPC472930
0.875	High Similarity	NPC470254
0.8737	High Similarity	NPC469400
0.8725	High Similarity	NPC51452
0.8713	High Similarity	NPC55872
0.87	High Similarity	NPC476240
0.87	High Similarity	NPC224720
0.87	High Similarity	NPC472924
0.87	High Similarity	NPC81530
0.87	High Similarity	NPC476223
0.8679	High Similarity	NPC472926
0.8673	High Similarity	NPC456
0.8673	High Similarity	NPC40765
0.8673	High Similarity	NPC7124
0.8673	High Similarity	NPC243525
0.8673	High Similarity	NPC472941
0.8667	High Similarity	NPC472928
0.8654	High Similarity	NPC286174
0.8654	High Similarity	NPC77947
0.8646	High Similarity	NPC107690
0.8614	High Similarity	NPC473424
0.86	High Similarity	NPC157787
0.8571	High Similarity	NPC129689
0.8571	High Similarity	NPC472932
0.8557	High Similarity	NPC243866
0.8557	High Similarity	NPC477435
0.8557	High Similarity	NPC477436
0.8529	High Similarity	NPC111323
0.8529	High Similarity	NPC70967
0.8529	High Similarity	NPC33973
0.8529	High Similarity	NPC311612
0.8526	High Similarity	NPC143767
0.8526	High Similarity	NPC131470
0.8526	High Similarity	NPC242864
0.8505	High Similarity	NPC472929
0.85	High Similarity	NPC235464
0.85	High Similarity	NPC166745
0.8491	Intermediate Similarity	NPC115303
0.8485	Intermediate Similarity	NPC95565
0.8469	Intermediate Similarity	NPC469406
0.8462	Intermediate Similarity	NPC473037
0.8462	Intermediate Similarity	NPC44063
0.8455	Intermediate Similarity	NPC472933
0.8454	Intermediate Similarity	NPC233116
0.8454	Intermediate Similarity	NPC168027
0.8454	Intermediate Similarity	NPC185936
0.8447	Intermediate Similarity	NPC216245
0.8447	Intermediate Similarity	NPC135854
0.8447	Intermediate Similarity	NPC470251
0.8447	Intermediate Similarity	NPC2436
0.8447	Intermediate Similarity	NPC235889
0.844	Intermediate Similarity	NPC472927
0.844	Intermediate Similarity	NPC471854
0.844	Intermediate Similarity	NPC472934
0.8438	Intermediate Similarity	NPC86319
0.8438	Intermediate Similarity	NPC275740
0.8431	Intermediate Similarity	NPC234892
0.8431	Intermediate Similarity	NPC87351
0.8431	Intermediate Similarity	NPC293753
0.8416	Intermediate Similarity	NPC144660
0.8416	Intermediate Similarity	NPC299971
0.8416	Intermediate Similarity	NPC307954
0.8416	Intermediate Similarity	NPC241221
0.8411	Intermediate Similarity	NPC475524
0.8411	Intermediate Similarity	NPC221144
0.8411	Intermediate Similarity	NPC100267
0.84	Intermediate Similarity	NPC253826
0.84	Intermediate Similarity	NPC107243
0.84	Intermediate Similarity	NPC18509
0.84	Intermediate Similarity	NPC122294
0.8396	Intermediate Similarity	NPC37116
0.8384	Intermediate Similarity	NPC477437
0.8384	Intermediate Similarity	NPC477438
0.8384	Intermediate Similarity	NPC48330
0.8384	Intermediate Similarity	NPC255809
0.8384	Intermediate Similarity	NPC134067
0.8367	Intermediate Similarity	NPC25750
0.8367	Intermediate Similarity	NPC206810
0.8365	Intermediate Similarity	NPC181265
0.8351	Intermediate Similarity	NPC183283
0.8351	Intermediate Similarity	NPC48010
0.835	Intermediate Similarity	NPC249187
0.835	Intermediate Similarity	NPC247957
0.8349	Intermediate Similarity	NPC148458
0.8333	Intermediate Similarity	NPC471722
0.8333	Intermediate Similarity	NPC124211
0.8333	Intermediate Similarity	NPC250109
0.8333	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC962
0.8317	Intermediate Similarity	NPC186810
0.8317	Intermediate Similarity	NPC478056
0.8317	Intermediate Similarity	NPC48647
0.8317	Intermediate Similarity	NPC114274
0.8317	Intermediate Similarity	NPC16021
0.8316	Intermediate Similarity	NPC28252
0.8316	Intermediate Similarity	NPC72133
0.8316	Intermediate Similarity	NPC322159
0.8316	Intermediate Similarity	NPC55309
0.8302	Intermediate Similarity	NPC2766
0.8302	Intermediate Similarity	NPC214644
0.83	Intermediate Similarity	NPC125622
0.83	Intermediate Similarity	NPC155676
0.83	Intermediate Similarity	NPC173272
0.83	Intermediate Similarity	NPC235053
0.8286	Intermediate Similarity	NPC185
0.8286	Intermediate Similarity	NPC475060
0.8286	Intermediate Similarity	NPC220229
0.8283	Intermediate Similarity	NPC196485
0.8283	Intermediate Similarity	NPC245972
0.8283	Intermediate Similarity	NPC8993
0.8283	Intermediate Similarity	NPC477439
0.8269	Intermediate Similarity	NPC96268
0.8269	Intermediate Similarity	NPC72255
0.8265	Intermediate Similarity	NPC475806
0.8265	Intermediate Similarity	NPC99380
0.8265	Intermediate Similarity	NPC23434
0.8265	Intermediate Similarity	NPC297265
0.8265	Intermediate Similarity	NPC26888
0.8265	Intermediate Similarity	NPC473998
0.8252	Intermediate Similarity	NPC281702
0.8252	Intermediate Similarity	NPC475320
0.8252	Intermediate Similarity	NPC477915
0.8252	Intermediate Similarity	NPC53222
0.8247	Intermediate Similarity	NPC309603
0.8247	Intermediate Similarity	NPC473999
0.8247	Intermediate Similarity	NPC123912
0.8247	Intermediate Similarity	NPC474889
0.8247	Intermediate Similarity	NPC54689
0.8247	Intermediate Similarity	NPC474245
0.8247	Intermediate Similarity	NPC155479
0.8241	Intermediate Similarity	NPC71348
0.8235	Intermediate Similarity	NPC266955
0.8235	Intermediate Similarity	NPC154072
0.8235	Intermediate Similarity	NPC144956
0.8235	Intermediate Similarity	NPC472972
0.8235	Intermediate Similarity	NPC472644
0.8235	Intermediate Similarity	NPC218383
0.823	Intermediate Similarity	NPC222688
0.8229	Intermediate Similarity	NPC136948
0.8229	Intermediate Similarity	NPC233836
0.8229	Intermediate Similarity	NPC187376
0.8229	Intermediate Similarity	NPC159046
0.8224	Intermediate Similarity	NPC197428
0.8218	Intermediate Similarity	NPC108078
0.8218	Intermediate Similarity	NPC69385
0.8218	Intermediate Similarity	NPC254496
0.8218	Intermediate Similarity	NPC57416
0.8218	Intermediate Similarity	NPC141401

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 NPC119601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1519
0.2-0.3	3809
0.3-0.4	2395
0.4-0.5	771
0.5-0.6	191
0.6-0.7	162
0.7-0.8	113
0.8-0.85	37
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD6402	Approved
0.8725	High Similarity	NPD7128	Approved
0.8725	High Similarity	NPD5739	Approved
0.8725	High Similarity	NPD6675	Approved
0.8558	High Similarity	NPD7320	Approved
0.8558	High Similarity	NPD6899	Approved
0.8558	High Similarity	NPD6881	Approved
0.8476	Intermediate Similarity	NPD6373	Approved
0.8476	Intermediate Similarity	NPD6372	Approved
0.8462	Intermediate Similarity	NPD5701	Approved
0.8462	Intermediate Similarity	NPD5697	Approved
0.8431	Intermediate Similarity	NPD5211	Phase 2
0.84	Intermediate Similarity	NPD4755	Approved
0.8396	Intermediate Similarity	NPD6883	Approved
0.8396	Intermediate Similarity	NPD7290	Approved
0.8396	Intermediate Similarity	NPD7102	Approved
0.8381	Intermediate Similarity	NPD6011	Approved
0.8318	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8318	Intermediate Similarity	NPD8130	Phase 1
0.8318	Intermediate Similarity	NPD6650	Approved
0.8318	Intermediate Similarity	NPD6869	Approved
0.8318	Intermediate Similarity	NPD6649	Approved
0.8318	Intermediate Similarity	NPD6617	Approved
0.8318	Intermediate Similarity	NPD6847	Approved
0.8302	Intermediate Similarity	NPD6013	Approved
0.8302	Intermediate Similarity	NPD6012	Approved
0.8302	Intermediate Similarity	NPD6014	Approved
0.8269	Intermediate Similarity	NPD5141	Approved
0.8247	Intermediate Similarity	NPD5328	Approved
0.8241	Intermediate Similarity	NPD8297	Approved
0.8241	Intermediate Similarity	NPD6882	Approved
0.8235	Intermediate Similarity	NPD5285	Approved
0.8235	Intermediate Similarity	NPD4700	Approved
0.8235	Intermediate Similarity	NPD4696	Approved
0.8235	Intermediate Similarity	NPD5286	Approved
0.8218	Intermediate Similarity	NPD6084	Phase 2
0.8218	Intermediate Similarity	NPD6083	Phase 2
0.82	Intermediate Similarity	NPD5695	Phase 3
0.8155	Intermediate Similarity	NPD5223	Approved
0.8119	Intermediate Similarity	NPD4697	Phase 3
0.8119	Intermediate Similarity	NPD5221	Approved
0.8119	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD5222	Approved
0.8081	Intermediate Similarity	NPD6079	Approved
0.8077	Intermediate Similarity	NPD5226	Approved
0.8077	Intermediate Similarity	NPD5225	Approved
0.8077	Intermediate Similarity	NPD4633	Approved
0.8077	Intermediate Similarity	NPD5224	Approved
0.8039	Intermediate Similarity	NPD5173	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7959	Intermediate Similarity	NPD6672	Approved
0.7959	Intermediate Similarity	NPD5737	Approved
0.7938	Intermediate Similarity	NPD5279	Phase 3
0.7879	Intermediate Similarity	NPD4753	Phase 2
0.7876	Intermediate Similarity	NPD6335	Approved
0.7857	Intermediate Similarity	NPD6274	Approved
0.785	Intermediate Similarity	NPD4767	Approved
0.785	Intermediate Similarity	NPD4768	Approved
0.7822	Intermediate Similarity	NPD4202	Approved
0.7807	Intermediate Similarity	NPD7100	Approved
0.7807	Intermediate Similarity	NPD7101	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7788	Intermediate Similarity	NPD6009	Approved
0.7788	Intermediate Similarity	NPD5696	Approved
0.7788	Intermediate Similarity	NPD6317	Approved
0.7755	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD4786	Approved
0.7723	Intermediate Similarity	NPD7515	Phase 2
0.7723	Intermediate Similarity	NPD5281	Approved
0.7723	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD6050	Approved
0.7719	Intermediate Similarity	NPD6314	Approved
0.7719	Intermediate Similarity	NPD6313	Approved
0.7714	Intermediate Similarity	NPD7640	Approved
0.7714	Intermediate Similarity	NPD7639	Approved
0.7706	Intermediate Similarity	NPD4730	Approved
0.7706	Intermediate Similarity	NPD4729	Approved
0.7706	Intermediate Similarity	NPD5128	Approved
0.77	Intermediate Similarity	NPD6904	Approved
0.77	Intermediate Similarity	NPD6080	Approved
0.77	Intermediate Similarity	NPD6673	Approved
0.7699	Intermediate Similarity	NPD6868	Approved
0.7685	Intermediate Similarity	NPD6008	Approved
0.7672	Intermediate Similarity	NPD6908	Approved
0.7672	Intermediate Similarity	NPD6909	Approved
0.7653	Intermediate Similarity	NPD5329	Approved
0.7624	Intermediate Similarity	NPD5692	Phase 3
0.7619	Intermediate Similarity	NPD7638	Approved
0.7586	Intermediate Similarity	NPD6319	Approved
0.7576	Intermediate Similarity	NPD7146	Approved
0.7576	Intermediate Similarity	NPD7334	Approved
0.7576	Intermediate Similarity	NPD4694	Approved
0.7576	Intermediate Similarity	NPD5330	Approved
0.7576	Intermediate Similarity	NPD7521	Approved
0.7576	Intermediate Similarity	NPD5690	Phase 2
0.7576	Intermediate Similarity	NPD6409	Approved
0.7576	Intermediate Similarity	NPD5280	Approved
0.7576	Intermediate Similarity	NPD6684	Approved
0.7573	Intermediate Similarity	NPD7748	Approved
0.7568	Intermediate Similarity	NPD5251	Approved
0.7568	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5247	Approved
0.7568	Intermediate Similarity	NPD5249	Phase 3
0.7568	Intermediate Similarity	NPD5135	Approved
0.7568	Intermediate Similarity	NPD5169	Approved
0.7568	Intermediate Similarity	NPD5250	Approved
0.7568	Intermediate Similarity	NPD5248	Approved
0.7568	Intermediate Similarity	NPD4634	Approved
0.7551	Intermediate Similarity	NPD3666	Approved
0.7551	Intermediate Similarity	NPD3665	Phase 1
0.7551	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD5694	Approved
0.7549	Intermediate Similarity	NPD5693	Phase 1
0.7542	Intermediate Similarity	NPD7604	Phase 2
0.7526	Intermediate Similarity	NPD3667	Approved
0.7524	Intermediate Similarity	NPD7902	Approved
0.7521	Intermediate Similarity	NPD5983	Phase 2
0.7521	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7479	Intermediate Similarity	NPD7492	Approved
0.7475	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6054	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7434	Intermediate Similarity	NPD6053	Discontinued
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6903	Approved
0.7417	Intermediate Similarity	NPD6616	Approved
0.7417	Intermediate Similarity	NPD6336	Discontinued
0.74	Intermediate Similarity	NPD6098	Approved
0.7387	Intermediate Similarity	NPD5168	Approved
0.7379	Intermediate Similarity	NPD8035	Phase 2
0.7379	Intermediate Similarity	NPD6411	Approved
0.7379	Intermediate Similarity	NPD8034	Phase 2
0.7355	Intermediate Similarity	NPD7078	Approved
0.7355	Intermediate Similarity	NPD8293	Discontinued
0.7353	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4223	Phase 3
0.7347	Intermediate Similarity	NPD4221	Approved
0.7311	Intermediate Similarity	NPD6370	Approved
0.7308	Intermediate Similarity	NPD5778	Approved
0.7308	Intermediate Similarity	NPD5779	Approved
0.7304	Intermediate Similarity	NPD5167	Approved
0.7295	Intermediate Similarity	NPD7736	Approved
0.7292	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3617	Approved
0.7248	Intermediate Similarity	NPD7632	Discontinued
0.7238	Intermediate Similarity	NPD7900	Approved
0.7238	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6016	Approved
0.7227	Intermediate Similarity	NPD6015	Approved
0.7184	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6101	Approved
0.717	Intermediate Similarity	NPD5654	Approved
0.7167	Intermediate Similarity	NPD5988	Approved
0.7157	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7131	Intermediate Similarity	NPD7507	Approved
0.7115	Intermediate Similarity	NPD5785	Approved
0.7115	Intermediate Similarity	NPD5207	Approved
0.71	Intermediate Similarity	NPD5362	Discontinued
0.71	Intermediate Similarity	NPD4788	Approved
0.7087	Intermediate Similarity	NPD5208	Approved
0.7075	Intermediate Similarity	NPD6001	Approved
0.7064	Intermediate Similarity	NPD6404	Discontinued
0.7059	Intermediate Similarity	NPD4690	Approved
0.7059	Intermediate Similarity	NPD5205	Approved
0.7059	Intermediate Similarity	NPD4623	Approved
0.7059	Intermediate Similarity	NPD4689	Approved
0.7059	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD4688	Approved
0.7059	Intermediate Similarity	NPD4138	Approved
0.7059	Intermediate Similarity	NPD5786	Approved
0.7059	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD5959	Approved
0.703	Intermediate Similarity	NPD3668	Phase 3
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6033	Approved
0.701	Intermediate Similarity	NPD6116	Phase 1
0.6991	Remote Similarity	NPD6412	Phase 2
0.6984	Remote Similarity	NPD7260	Phase 2
0.6981	Remote Similarity	NPD5133	Approved
0.6972	Remote Similarity	NPD4225	Approved
0.6961	Remote Similarity	NPD5363	Approved
0.6961	Remote Similarity	NPD1694	Approved
0.6961	Remote Similarity	NPD1696	Phase 3
0.696	Remote Similarity	NPD7319	Approved
0.6907	Remote Similarity	NPD6117	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