NPASS Compound

Structure

CID23434 OpenBabel06191715352D 35 38 0 0 1 0 0 0 0 0999 V2000 2.8619 3.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2105 3.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4572 1.7364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3803 -2.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -2.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8057 2.0869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0812 2.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9350 3.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7326 2.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 2.4374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6900 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 0.9746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5355 -1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2243 -1.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5702 3.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3800 -1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9751 0.0000 C 0 0 1 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 -2.5554 1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0906 -1.9618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 4.0429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4972 2.7879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 20 10 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 28 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 33 1 6 0 0 0 26 30 1 6 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.37
Volume:	537.758
LogP:	5.158
LogD:	4.218
LogS:	-4.598
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	4.994
Fsp3:	0.839
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:	-5.274
MDCK Permeability:	9.42792757996358e-06
Pgp-inhibitor:	0.337
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.464
30% Bioavailability (F30%):	0.154

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	93.61896514892578%
Volume Distribution (VD):	0.692
Pgp-substrate:	3.1399295330047607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.49
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	3.651
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.414
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.086
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.035
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC23434

Natural Product ID:	NPC23434
*Common Name:**	Tumulosic Acid
IUPAC Name:	(2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	Tumulosic Acid
Standard InCHIKey:	XADJANKGURNTIA-YEXRKOARSA-N
Standard InCHI:	InChI=1S/C31H50O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-26,32-33H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,25+,26+,29-,30-,31+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461484
PubChem CID:	12314446
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[505047]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[505047]
NPT2	Others	Unspecified		Activity	=	22.7	%	PMID[505047]
NPT2	Others	Unspecified		Activity	=	64.9	%	PMID[505047]
NPT2	Others	Unspecified		Activity	=	90.5	%	PMID[505047]

☑ 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 NPC23434 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	169
0.1-0.2	1211
0.2-0.3	5350
0.3-0.4	14864
0.4-0.5	7300
0.5-0.6	5773
0.6-0.7	5679
0.7-0.8	2023
0.8-0.85	233
0.85-0.9	51
0.9-0.95	32
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC222845
0.9659	High Similarity	NPC45324
0.9659	High Similarity	NPC162001
0.9659	High Similarity	NPC184848
0.9659	High Similarity	NPC69548
0.9655	High Similarity	NPC470375
0.9655	High Similarity	NPC470376
0.9535	High Similarity	NPC54689
0.9419	High Similarity	NPC242864
0.9412	High Similarity	NPC28252
0.9412	High Similarity	NPC55309
0.9412	High Similarity	NPC212843
0.9341	High Similarity	NPC477813
0.9341	High Similarity	NPC186810
0.9341	High Similarity	NPC48647
0.9302	High Similarity	NPC187376
0.9302	High Similarity	NPC312215
0.9302	High Similarity	NPC233836
0.9302	High Similarity	NPC159046
0.9222	High Similarity	NPC48330
0.9213	High Similarity	NPC152897
0.9213	High Similarity	NPC66429
0.9213	High Similarity	NPC243866
0.9205	High Similarity	NPC469400
0.9195	High Similarity	NPC183546
0.9195	High Similarity	NPC294480
0.9121	High Similarity	NPC173272
0.9101	High Similarity	NPC297265
0.9101	High Similarity	NPC154101
0.9091	High Similarity	NPC474704
0.9091	High Similarity	NPC155479
0.9091	High Similarity	NPC77168
0.9091	High Similarity	NPC475921
0.9091	High Similarity	NPC474889
0.9091	High Similarity	NPC84271
0.9091	High Similarity	NPC102414
0.908	High Similarity	NPC474684
0.908	High Similarity	NPC142361
0.9011	High Similarity	NPC263347
0.8989	High Similarity	NPC111585
0.8989	High Similarity	NPC148414
0.8989	High Similarity	NPC175628
0.8989	High Similarity	NPC46281
0.8977	High Similarity	NPC48866
0.8977	High Similarity	NPC247406
0.8913	High Similarity	NPC155676
0.8913	High Similarity	NPC95565
0.8901	High Similarity	NPC166906
0.8901	High Similarity	NPC469406
0.8889	High Similarity	NPC212301
0.8889	High Similarity	NPC26888
0.8889	High Similarity	NPC86266
0.8889	High Similarity	NPC189520
0.8889	High Similarity	NPC110657
0.8854	High Similarity	NPC477812
0.8804	High Similarity	NPC317586
0.8804	High Similarity	NPC469599
0.8804	High Similarity	NPC470016
0.8791	High Similarity	NPC470224
0.8791	High Similarity	NPC206810
0.8791	High Similarity	NPC141497
0.8791	High Similarity	NPC107674
0.8791	High Similarity	NPC170220
0.8778	High Similarity	NPC123854
0.8778	High Similarity	NPC44240
0.8778	High Similarity	NPC471896
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC72133
0.875	High Similarity	NPC155011
0.871	High Similarity	NPC96859
0.871	High Similarity	NPC120708
0.871	High Similarity	NPC328162
0.871	High Similarity	NPC305483
0.8696	High Similarity	NPC49670
0.8696	High Similarity	NPC111015
0.8681	High Similarity	NPC45269
0.8681	High Similarity	NPC150383
0.866	High Similarity	NPC472228
0.866	High Similarity	NPC472227
0.8646	High Similarity	NPC195290
0.8646	High Similarity	NPC204450
0.8636	High Similarity	NPC474218
0.8632	High Similarity	NPC316964
0.8617	High Similarity	NPC57416
0.8617	High Similarity	NPC320306
0.8617	High Similarity	NPC107243
0.8602	High Similarity	NPC255809
0.8587	High Similarity	NPC25750
0.8571	High Similarity	NPC477872
0.8571	High Similarity	NPC7260
0.8571	High Similarity	NPC120968
0.8571	High Similarity	NPC273621
0.8571	High Similarity	NPC20388
0.8571	High Similarity	NPC18872
0.8571	High Similarity	NPC210037
0.8571	High Similarity	NPC290614
0.8571	High Similarity	NPC227467
0.8557	High Similarity	NPC236390
0.8557	High Similarity	NPC140723
0.8557	High Similarity	NPC55872
0.8556	High Similarity	NPC143767
0.8556	High Similarity	NPC471722
0.8556	High Similarity	NPC131470
0.8556	High Similarity	NPC471724
0.8556	High Similarity	NPC474719
0.8539	High Similarity	NPC73038
0.8539	High Similarity	NPC2783
0.8526	High Similarity	NPC477854
0.8526	High Similarity	NPC10364
0.8523	High Similarity	NPC82902
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC477853
0.8495	Intermediate Similarity	NPC7165
0.8495	Intermediate Similarity	NPC471720
0.8495	Intermediate Similarity	NPC159410
0.8485	Intermediate Similarity	NPC42847
0.8485	Intermediate Similarity	NPC64844
0.8478	Intermediate Similarity	NPC187722
0.8478	Intermediate Similarity	NPC105189
0.8478	Intermediate Similarity	NPC107690
0.8469	Intermediate Similarity	NPC96268
0.8469	Intermediate Similarity	NPC28656
0.8462	Intermediate Similarity	NPC476733
0.8462	Intermediate Similarity	NPC215029
0.8462	Intermediate Similarity	NPC128496
0.8462	Intermediate Similarity	NPC474679
0.8462	Intermediate Similarity	NPC214387
0.8462	Intermediate Similarity	NPC25906
0.8462	Intermediate Similarity	NPC275740
0.8462	Intermediate Similarity	NPC477943
0.8462	Intermediate Similarity	NPC290972
0.8462	Intermediate Similarity	NPC86319
0.8462	Intermediate Similarity	NPC64872
0.8454	Intermediate Similarity	NPC293753
0.8454	Intermediate Similarity	NPC234892
0.8454	Intermediate Similarity	NPC22388
0.8444	Intermediate Similarity	NPC96496
0.8444	Intermediate Similarity	NPC269360
0.8444	Intermediate Similarity	NPC138756
0.8444	Intermediate Similarity	NPC33768
0.8444	Intermediate Similarity	NPC167877
0.8444	Intermediate Similarity	NPC477926
0.8444	Intermediate Similarity	NPC264005
0.8444	Intermediate Similarity	NPC317590
0.8438	Intermediate Similarity	NPC218383
0.8438	Intermediate Similarity	NPC154072
0.8438	Intermediate Similarity	NPC327431
0.8438	Intermediate Similarity	NPC205899
0.8427	Intermediate Similarity	NPC294438
0.8427	Intermediate Similarity	NPC264317
0.8421	Intermediate Similarity	NPC475894
0.8421	Intermediate Similarity	NPC108078
0.8421	Intermediate Similarity	NPC122294
0.8421	Intermediate Similarity	NPC18319
0.8421	Intermediate Similarity	NPC190554
0.8421	Intermediate Similarity	NPC43747
0.8409	Intermediate Similarity	NPC245866
0.8404	Intermediate Similarity	NPC174948
0.8404	Intermediate Similarity	NPC473648
0.8404	Intermediate Similarity	NPC241156
0.8404	Intermediate Similarity	NPC318282
0.8404	Intermediate Similarity	NPC205173
0.8404	Intermediate Similarity	NPC472485
0.8404	Intermediate Similarity	NPC20546
0.8404	Intermediate Similarity	NPC279974
0.8404	Intermediate Similarity	NPC469995
0.8404	Intermediate Similarity	NPC173875
0.8391	Intermediate Similarity	NPC201912
0.8391	Intermediate Similarity	NPC473420
0.8391	Intermediate Similarity	NPC38350
0.8387	Intermediate Similarity	NPC158059
0.8387	Intermediate Similarity	NPC229281
0.8387	Intermediate Similarity	NPC477855
0.8387	Intermediate Similarity	NPC202728
0.8387	Intermediate Similarity	NPC475255
0.8387	Intermediate Similarity	NPC118519
0.8387	Intermediate Similarity	NPC470254
0.8384	Intermediate Similarity	NPC278628
0.8384	Intermediate Similarity	NPC475494
0.8384	Intermediate Similarity	NPC231530
0.837	Intermediate Similarity	NPC130278
0.837	Intermediate Similarity	NPC193750
0.837	Intermediate Similarity	NPC171441
0.837	Intermediate Similarity	NPC477147
0.837	Intermediate Similarity	NPC183283
0.837	Intermediate Similarity	NPC477149
0.837	Intermediate Similarity	NPC291028
0.837	Intermediate Similarity	NPC191684
0.8367	Intermediate Similarity	NPC159442
0.8352	Intermediate Similarity	NPC16377
0.8352	Intermediate Similarity	NPC328313
0.8352	Intermediate Similarity	NPC52169
0.8352	Intermediate Similarity	NPC182797
0.8351	Intermediate Similarity	NPC473514
0.8351	Intermediate Similarity	NPC302537
0.8351	Intermediate Similarity	NPC474327
0.8351	Intermediate Similarity	NPC163372
0.8333	Intermediate Similarity	NPC474970
0.8333	Intermediate Similarity	NPC472491
0.8333	Intermediate Similarity	NPC469994

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 NPC23434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1635
0.2-0.3	4043
0.3-0.4	2262
0.4-0.5	585
0.5-0.6	148
0.6-0.7	165
0.7-0.8	150
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD6399	Phase 3
0.8427	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD4202	Approved
0.8384	Intermediate Similarity	NPD6675	Approved
0.8384	Intermediate Similarity	NPD7128	Approved
0.8384	Intermediate Similarity	NPD5739	Approved
0.8384	Intermediate Similarity	NPD6402	Approved
0.8333	Intermediate Similarity	NPD3618	Phase 1
0.8317	Intermediate Similarity	NPD6372	Approved
0.8317	Intermediate Similarity	NPD6373	Approved
0.8315	Intermediate Similarity	NPD4786	Approved
0.828	Intermediate Similarity	NPD8035	Phase 2
0.828	Intermediate Similarity	NPD5281	Approved
0.828	Intermediate Similarity	NPD5284	Approved
0.828	Intermediate Similarity	NPD8034	Phase 2
0.8261	Intermediate Similarity	NPD5328	Approved
0.8229	Intermediate Similarity	NPD4755	Approved
0.8218	Intermediate Similarity	NPD6899	Approved
0.8218	Intermediate Similarity	NPD6881	Approved
0.8218	Intermediate Similarity	NPD7320	Approved
0.8155	Intermediate Similarity	NPD6649	Approved
0.8155	Intermediate Similarity	NPD6650	Approved
0.8119	Intermediate Similarity	NPD5701	Approved
0.8119	Intermediate Similarity	NPD5697	Approved
0.8111	Intermediate Similarity	NPD3133	Approved
0.8111	Intermediate Similarity	NPD3666	Approved
0.8111	Intermediate Similarity	NPD3665	Phase 1
0.809	Intermediate Similarity	NPD3667	Approved
0.8085	Intermediate Similarity	NPD7515	Phase 2
0.8085	Intermediate Similarity	NPD6079	Approved
0.8061	Intermediate Similarity	NPD4700	Approved
0.8061	Intermediate Similarity	NPD4696	Approved
0.8061	Intermediate Similarity	NPD5285	Approved
0.8061	Intermediate Similarity	NPD5286	Approved
0.8058	Intermediate Similarity	NPD6883	Approved
0.8058	Intermediate Similarity	NPD7102	Approved
0.8058	Intermediate Similarity	NPD7290	Approved
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD6011	Approved
0.8021	Intermediate Similarity	NPD5695	Phase 3
0.7981	Intermediate Similarity	NPD6617	Approved
0.7981	Intermediate Similarity	NPD8130	Phase 1
0.7981	Intermediate Similarity	NPD6847	Approved
0.7981	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD6869	Approved
0.798	Intermediate Similarity	NPD5223	Approved
0.7961	Intermediate Similarity	NPD6012	Approved
0.7961	Intermediate Similarity	NPD6014	Approved
0.7961	Intermediate Similarity	NPD6013	Approved
0.7938	Intermediate Similarity	NPD4697	Phase 3
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7931	Intermediate Similarity	NPD6116	Phase 1
0.7905	Intermediate Similarity	NPD8297	Approved
0.7905	Intermediate Similarity	NPD6882	Approved
0.79	Intermediate Similarity	NPD5225	Approved
0.79	Intermediate Similarity	NPD5211	Phase 2
0.79	Intermediate Similarity	NPD4633	Approved
0.79	Intermediate Similarity	NPD5226	Approved
0.79	Intermediate Similarity	NPD5224	Approved
0.7872	Intermediate Similarity	NPD4753	Phase 2
0.7865	Intermediate Similarity	NPD7525	Registered
0.7857	Intermediate Similarity	NPD7902	Approved
0.7835	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD4754	Approved
0.7822	Intermediate Similarity	NPD5174	Approved
0.7822	Intermediate Similarity	NPD5175	Approved
0.7816	Intermediate Similarity	NPD6117	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD5696	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7755	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5221	Approved
0.7755	Intermediate Similarity	NPD5222	Approved
0.7745	Intermediate Similarity	NPD5141	Approved
0.7742	Intermediate Similarity	NPD5279	Phase 3
0.7732	Intermediate Similarity	NPD7748	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4221	Approved
0.7677	Intermediate Similarity	NPD5173	Approved
0.767	Intermediate Similarity	NPD4768	Approved
0.767	Intermediate Similarity	NPD6008	Approved
0.767	Intermediate Similarity	NPD4767	Approved
0.7664	Intermediate Similarity	NPD4632	Approved
0.7653	Intermediate Similarity	NPD5210	Approved
0.7653	Intermediate Similarity	NPD4629	Approved
0.764	Intermediate Similarity	NPD6118	Approved
0.764	Intermediate Similarity	NPD6114	Approved
0.764	Intermediate Similarity	NPD6115	Approved
0.764	Intermediate Similarity	NPD6697	Approved
0.7634	Intermediate Similarity	NPD5329	Approved
0.7614	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4788	Approved
0.7586	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4692	Approved
0.7582	Intermediate Similarity	NPD4139	Approved
0.7579	Intermediate Similarity	NPD6672	Approved
0.7579	Intermediate Similarity	NPD5737	Approved
0.7553	Intermediate Similarity	NPD5690	Phase 2
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6098	Approved
0.7553	Intermediate Similarity	NPD5280	Approved
0.7553	Intermediate Similarity	NPD4694	Approved
0.7551	Intermediate Similarity	NPD7900	Approved
0.7551	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6335	Approved
0.7527	Intermediate Similarity	NPD4197	Approved
0.7527	Intermediate Similarity	NPD3668	Phase 3
0.7526	Intermediate Similarity	NPD6050	Approved
0.7524	Intermediate Similarity	NPD4730	Approved
0.7524	Intermediate Similarity	NPD4729	Approved
0.7524	Intermediate Similarity	NPD5128	Approved
0.7523	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7477	Intermediate Similarity	NPD7101	Approved
0.7477	Intermediate Similarity	NPD7100	Approved
0.7473	Intermediate Similarity	NPD4748	Discontinued
0.7455	Intermediate Similarity	NPD6009	Approved
0.7455	Intermediate Similarity	NPD6317	Approved
0.7423	Intermediate Similarity	NPD5207	Approved
0.7423	Intermediate Similarity	NPD5692	Phase 3
0.7387	Intermediate Similarity	NPD6314	Approved
0.7387	Intermediate Similarity	NPD6313	Approved
0.7383	Intermediate Similarity	NPD5249	Phase 3
0.7383	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5247	Approved
0.7383	Intermediate Similarity	NPD5248	Approved
0.7383	Intermediate Similarity	NPD4634	Approved
0.7383	Intermediate Similarity	NPD5250	Approved
0.7383	Intermediate Similarity	NPD5135	Approved
0.7383	Intermediate Similarity	NPD5251	Approved
0.7383	Intermediate Similarity	NPD5169	Approved
0.7374	Intermediate Similarity	NPD6001	Approved
0.7368	Intermediate Similarity	NPD4690	Approved
0.7368	Intermediate Similarity	NPD5205	Approved
0.7368	Intermediate Similarity	NPD4693	Phase 3
0.7368	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD4138	Approved
0.7368	Intermediate Similarity	NPD4688	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.7347	Intermediate Similarity	NPD5694	Approved
0.7345	Intermediate Similarity	NPD6909	Approved
0.7345	Intermediate Similarity	NPD6908	Approved
0.7345	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5215	Approved
0.7315	Intermediate Similarity	NPD5127	Approved
0.7315	Intermediate Similarity	NPD5217	Approved
0.7315	Intermediate Similarity	NPD5216	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7283	Intermediate Similarity	NPD5368	Approved
0.7264	Intermediate Similarity	NPD6412	Phase 2
0.7257	Intermediate Similarity	NPD6319	Approved
0.7253	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5362	Discontinued
0.7217	Intermediate Similarity	NPD7604	Phase 2
0.7216	Intermediate Similarity	NPD5208	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7207	Intermediate Similarity	NPD6868	Approved
0.7204	Intermediate Similarity	NPD5369	Approved
0.7193	Intermediate Similarity	NPD5983	Phase 2
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7159	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4243	Approved
0.7159	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6051	Approved
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6435	Approved
0.7128	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD4270	Approved
0.7117	Intermediate Similarity	NPD5167	Approved
0.7105	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6059	Approved
0.7094	Intermediate Similarity	NPD6336	Discontinued
0.7094	Intermediate Similarity	NPD6616	Approved
0.7071	Intermediate Similarity	NPD4096	Approved
0.7065	Intermediate Similarity	NPD3617	Approved
0.7045	Intermediate Similarity	NPD4245	Approved
0.7045	Intermediate Similarity	NPD4244	Approved
0.7037	Intermediate Similarity	NPD5168	Approved
0.7034	Intermediate Similarity	NPD8293	Discontinued
0.7034	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD4784	Approved
0.6989	Remote Similarity	NPD4195	Approved
0.6989	Remote Similarity	NPD7645	Phase 2

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