NPASS Compound

Structure

NPC469406 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 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 -1.5388 -0.5000 0.0000 C 0 0 0 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 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 -0.0000 -1.0000 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 -3.4743 -6.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 10 11 1 0 0 0 0 10 23 2 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 0 0 0 0 20 9 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 4 1 1 0 0 0 29 30 1 1 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.26
Volume:	416.686
LogP:	5.382
LogD:	4.477
LogS:	-5.327
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.653
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914
MDCK Permeability:	2.267184572701808e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	88.18827056884766%
Volume Distribution (VD):	0.626
Pgp-substrate:	7.025320053100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.422
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.514
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	15.575
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.264
Maximum Recommended Daily Dose:	0.596
Skin Sensitization:	0.115
Carcinogencity:	0.205
Eye Corrosion:	0.014
Eye Irritation:	0.045
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC469406

Natural Product ID:	NPC469406
*Common Name:**	(20Zeta)-3Alpha,16Alpha,27-Trihydroxylanosta-7,9(11),24-Trien-21-Oic Acid
IUPAC Name:	(Z,2R)-7-hydroxy-2-[(3R,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:	16alpha,27-dihydroxydehydrotrametenoic acid
Standard InCHIKey:	NBYDYPSPSIPINS-CJAOMCBOSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(18-31)8-7-9-20(26(33)34)21-12-16-30(6)23-10-11-24-27(2,3)25(32)14-15-28(24,4)22(23)13-17-29(21,30)5/h8,10,13,20-21,24-25,31-32H,7,9,11-12,14-18H2,1-6H3,(H,33,34)/b19-8-/t20-,21-,24+,25-,28-,29-,30+/m1/s1
SMILES:	CC(=CCCC(C1CCC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C)C(=O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077993
PubChem CID:	46882716
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
IC50	3
Others	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	76000.0	nM	PMID[480200]
NPT80	Cell Line	Raji	Homo sapiens	Inhibition	=	70.0	%	PMID[480200]
NPT2	Others	Unspecified		IC50	=	269.0	molar ratio	PMID[480200]
NPT2	Others	Unspecified		Inhibition	=	90.1	%	PMID[480200]
NPT2	Others	Unspecified		Inhibition	=	69.2	%	PMID[480200]
NPT2	Others	Unspecified		Inhibition	=	20.8	%	PMID[480200]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[480200]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	96800.0	nM	PMID[480200]

☑ 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 NPC469406 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	159
0.1-0.2	870
0.2-0.3	3900
0.3-0.4	10967
0.4-0.5	11943
0.5-0.6	6867
0.6-0.7	5304
0.7-0.8	2266
0.8-0.85	276
0.85-0.9	121
0.9-0.95	19
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC48647
0.954	High Similarity	NPC102414
0.954	High Similarity	NPC77168
0.954	High Similarity	NPC84271
0.9432	High Similarity	NPC469400
0.9348	High Similarity	NPC186810
0.931	High Similarity	NPC159046
0.931	High Similarity	NPC187376
0.931	High Similarity	NPC233836
0.9231	High Similarity	NPC222845
0.9231	High Similarity	NPC45324
0.9231	High Similarity	NPC162001
0.9222	High Similarity	NPC214697
0.9205	High Similarity	NPC242864
0.9195	High Similarity	NPC28252
0.9195	High Similarity	NPC55309
0.9111	High Similarity	NPC212948
0.9101	High Similarity	NPC475921
0.9101	High Similarity	NPC474704
0.9091	High Similarity	NPC142361
0.9091	High Similarity	NPC474684
0.9032	High Similarity	NPC320306
0.9	High Similarity	NPC111585
0.9	High Similarity	NPC175628
0.9	High Similarity	NPC148414
0.8966	High Similarity	NPC165064
0.8936	High Similarity	NPC235464
0.8936	High Similarity	NPC477813
0.8936	High Similarity	NPC166745
0.8936	High Similarity	NPC471717
0.8925	High Similarity	NPC250757
0.8925	High Similarity	NPC155676
0.8925	High Similarity	NPC301534
0.8925	High Similarity	NPC472941
0.8925	High Similarity	NPC456
0.8913	High Similarity	NPC49670
0.8901	High Similarity	NPC26888
0.8901	High Similarity	NPC23434
0.8901	High Similarity	NPC297265
0.8901	High Similarity	NPC189520
0.8889	High Similarity	NPC214387
0.8889	High Similarity	NPC474889
0.8864	High Similarity	NPC474083
0.8854	High Similarity	NPC293753
0.8854	High Similarity	NPC234892
0.8842	High Similarity	NPC327431
0.883	High Similarity	NPC141401
0.8817	High Similarity	NPC469995
0.8817	High Similarity	NPC173875
0.8817	High Similarity	NPC318282
0.8817	High Similarity	NPC174948
0.8804	High Similarity	NPC470376
0.8804	High Similarity	NPC470375
0.8804	High Similarity	NPC69454
0.8804	High Similarity	NPC66429
0.8804	High Similarity	NPC152897
0.8804	High Similarity	NPC472942
0.8791	High Similarity	NPC69622
0.8791	High Similarity	NPC477147
0.8791	High Similarity	NPC471896
0.8791	High Similarity	NPC477149
0.8764	High Similarity	NPC473226
0.8764	High Similarity	NPC94755
0.8764	High Similarity	NPC155011
0.8736	High Similarity	NPC202389
0.8723	High Similarity	NPC173272
0.8723	High Similarity	NPC190713
0.8723	High Similarity	NPC328371
0.8723	High Similarity	NPC7124
0.8723	High Similarity	NPC249954
0.871	High Similarity	NPC166906
0.8696	High Similarity	NPC107690
0.8696	High Similarity	NPC233116
0.8696	High Similarity	NPC473998
0.8696	High Similarity	NPC63748
0.8696	High Similarity	NPC86266
0.8696	High Similarity	NPC212301
0.8696	High Similarity	NPC45269
0.8696	High Similarity	NPC110657
0.8681	High Similarity	NPC262858
0.8681	High Similarity	NPC472240
0.8681	High Similarity	NPC473999
0.8681	High Similarity	NPC309603
0.8652	High Similarity	NPC471224
0.8646	High Similarity	NPC287833
0.8646	High Similarity	NPC51370
0.8646	High Similarity	NPC266955
0.8636	High Similarity	NPC69279
0.8636	High Similarity	NPC310470
0.8636	High Similarity	NPC83569
0.8632	High Similarity	NPC253826
0.8632	High Similarity	NPC122294
0.8617	High Similarity	NPC259286
0.8617	High Similarity	NPC48330
0.8617	High Similarity	NPC470016
0.8617	High Similarity	NPC317586
0.8617	High Similarity	NPC184848
0.8617	High Similarity	NPC69548
0.8617	High Similarity	NPC263347
0.8602	High Similarity	NPC141497
0.8602	High Similarity	NPC107674
0.8602	High Similarity	NPC472930
0.8602	High Similarity	NPC243866
0.8602	High Similarity	NPC470254
0.8602	High Similarity	NPC470224
0.8602	High Similarity	NPC170220
0.8587	High Similarity	NPC46281
0.8587	High Similarity	NPC48010
0.8571	High Similarity	NPC471722
0.8571	High Similarity	NPC24816
0.8571	High Similarity	NPC247406
0.8571	High Similarity	NPC48866
0.8571	High Similarity	NPC16377
0.8557	High Similarity	NPC163372
0.8557	High Similarity	NPC472924
0.8557	High Similarity	NPC99411
0.8557	High Similarity	NPC115899
0.8557	High Similarity	NPC302537
0.8557	High Similarity	NPC282524
0.8556	High Similarity	NPC73038
0.8556	High Similarity	NPC82979
0.8556	High Similarity	NPC72133
0.8556	High Similarity	NPC322159
0.8542	High Similarity	NPC16021
0.8542	High Similarity	NPC197386
0.8542	High Similarity	NPC103051
0.8542	High Similarity	NPC57079
0.8542	High Similarity	NPC108368
0.8539	High Similarity	NPC231310
0.8526	High Similarity	NPC235053
0.8526	High Similarity	NPC120708
0.8526	High Similarity	NPC305483
0.8526	High Similarity	NPC328162
0.8526	High Similarity	NPC96859
0.8511	High Similarity	NPC474922
0.8511	High Similarity	NPC7165
0.8511	High Similarity	NPC474690
0.8511	High Similarity	NPC299100
0.8511	High Similarity	NPC80365
0.8511	High Similarity	NPC8993
0.8511	High Similarity	NPC292793
0.8511	High Similarity	NPC471720
0.8511	High Similarity	NPC184870
0.85	High Similarity	NPC472925
0.8495	Intermediate Similarity	NPC204341
0.8495	Intermediate Similarity	NPC475806
0.8495	Intermediate Similarity	NPC301244
0.8485	Intermediate Similarity	NPC477812
0.8478	Intermediate Similarity	NPC54689
0.8478	Intermediate Similarity	NPC472971
0.8478	Intermediate Similarity	NPC275740
0.8478	Intermediate Similarity	NPC95246
0.8478	Intermediate Similarity	NPC86319
0.8478	Intermediate Similarity	NPC472970
0.8478	Intermediate Similarity	NPC161751
0.8478	Intermediate Similarity	NPC474972
0.8478	Intermediate Similarity	NPC128496
0.8478	Intermediate Similarity	NPC146554
0.8478	Intermediate Similarity	NPC155479
0.8469	Intermediate Similarity	NPC136289
0.8469	Intermediate Similarity	NPC308726
0.8469	Intermediate Similarity	NPC119601
0.8469	Intermediate Similarity	NPC204450
0.8469	Intermediate Similarity	NPC195290
0.8462	Intermediate Similarity	NPC96496
0.8462	Intermediate Similarity	NPC312215
0.8454	Intermediate Similarity	NPC144660
0.8454	Intermediate Similarity	NPC299971
0.8454	Intermediate Similarity	NPC307954
0.8454	Intermediate Similarity	NPC476274
0.8438	Intermediate Similarity	NPC99726
0.8438	Intermediate Similarity	NPC107243
0.8438	Intermediate Similarity	NPC108078
0.8438	Intermediate Similarity	NPC475894
0.8421	Intermediate Similarity	NPC476174
0.8421	Intermediate Similarity	NPC88310
0.8421	Intermediate Similarity	NPC53565
0.8421	Intermediate Similarity	NPC271195
0.8421	Intermediate Similarity	NPC127063
0.8421	Intermediate Similarity	NPC279974
0.8421	Intermediate Similarity	NPC37646
0.8421	Intermediate Similarity	NPC180950
0.8416	Intermediate Similarity	NPC295244
0.8409	Intermediate Similarity	NPC473420
0.8409	Intermediate Similarity	NPC201912
0.8409	Intermediate Similarity	NPC38350
0.8409	Intermediate Similarity	NPC4166
0.8404	Intermediate Similarity	NPC476304
0.8404	Intermediate Similarity	NPC477855
0.8404	Intermediate Similarity	NPC38232
0.84	Intermediate Similarity	NPC323834
0.8391	Intermediate Similarity	NPC274996
0.8391	Intermediate Similarity	NPC196827
0.8387	Intermediate Similarity	NPC20388
0.8387	Intermediate Similarity	NPC191684
0.8387	Intermediate Similarity	NPC123854
0.8384	Intermediate Similarity	NPC236390
0.8384	Intermediate Similarity	NPC475050
0.837	Intermediate Similarity	NPC44181
0.837	Intermediate Similarity	NPC131470

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 NPC469406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1140
0.2-0.3	3687
0.3-0.4	2720
0.4-0.5	900
0.5-0.6	232
0.6-0.7	190
0.7-0.8	135
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD4786	Approved
0.828	Intermediate Similarity	NPD5328	Approved
0.8242	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD6399	Phase 3
0.8152	Intermediate Similarity	NPD5279	Phase 3
0.8152	Intermediate Similarity	NPD3618	Phase 1
0.8111	Intermediate Similarity	NPD3667	Approved
0.8105	Intermediate Similarity	NPD7515	Phase 2
0.8105	Intermediate Similarity	NPD6079	Approved
0.8081	Intermediate Similarity	NPD7639	Approved
0.8081	Intermediate Similarity	NPD7640	Approved
0.798	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD5284	Approved
0.7917	Intermediate Similarity	NPD5281	Approved
0.7865	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD7128	Approved
0.7864	Intermediate Similarity	NPD5739	Approved
0.7864	Intermediate Similarity	NPD6675	Approved
0.7835	Intermediate Similarity	NPD4202	Approved
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD5222	Approved
0.7755	Intermediate Similarity	NPD7748	Approved
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7742	Intermediate Similarity	NPD3133	Approved
0.7742	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD3666	Approved
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7732	Intermediate Similarity	NPD6411	Approved
0.7723	Intermediate Similarity	NPD6404	Discontinued
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD7320	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.77	Intermediate Similarity	NPD6083	Phase 2
0.77	Intermediate Similarity	NPD4755	Approved
0.77	Intermediate Similarity	NPD5173	Approved
0.77	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD7525	Registered
0.7677	Intermediate Similarity	NPD5695	Phase 3
0.7653	Intermediate Similarity	NPD5779	Approved
0.7653	Intermediate Similarity	NPD5778	Approved
0.7642	Intermediate Similarity	NPD6372	Approved
0.7642	Intermediate Similarity	NPD6373	Approved
0.764	Intermediate Similarity	NPD6117	Approved
0.7636	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD5701	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.7604	Intermediate Similarity	NPD5737	Approved
0.7604	Intermediate Similarity	NPD6672	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD4694	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD5280	Approved
0.7579	Intermediate Similarity	NPD6684	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7556	Intermediate Similarity	NPD6116	Phase 1
0.7553	Intermediate Similarity	NPD3668	Phase 3
0.7551	Intermediate Similarity	NPD6050	Approved
0.7551	Intermediate Similarity	NPD7637	Suspended
0.7549	Intermediate Similarity	NPD4696	Approved
0.7549	Intermediate Similarity	NPD4700	Approved
0.7549	Intermediate Similarity	NPD5285	Approved
0.7549	Intermediate Similarity	NPD5286	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7528	Intermediate Similarity	NPD7339	Approved
0.7528	Intermediate Similarity	NPD6942	Approved
0.7526	Intermediate Similarity	NPD6101	Approved
0.7526	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD4753	Phase 2
0.7525	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7476	Intermediate Similarity	NPD5223	Approved
0.7473	Intermediate Similarity	NPD6115	Approved
0.7473	Intermediate Similarity	NPD6118	Approved
0.7473	Intermediate Similarity	NPD6697	Approved
0.7473	Intermediate Similarity	NPD6114	Approved
0.7449	Intermediate Similarity	NPD5692	Phase 3
0.7447	Intermediate Similarity	NPD5362	Discontinued
0.7431	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6903	Approved
0.7416	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5225	Approved
0.7404	Intermediate Similarity	NPD7632	Discontinued
0.7404	Intermediate Similarity	NPD5226	Approved
0.7404	Intermediate Similarity	NPD5224	Approved
0.7404	Intermediate Similarity	NPD4633	Approved
0.7374	Intermediate Similarity	NPD5694	Approved
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4221	Approved
0.734	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD5174	Approved
0.7333	Intermediate Similarity	NPD5175	Approved
0.7333	Intermediate Similarity	NPD4754	Approved
0.7333	Intermediate Similarity	NPD8264	Approved
0.7327	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5329	Approved
0.7282	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD5207	Approved
0.7253	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6868	Approved
0.7228	Intermediate Similarity	NPD7900	Approved
0.7228	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5733	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7216	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6098	Approved
0.7216	Intermediate Similarity	NPD5690	Phase 2
0.7207	Intermediate Similarity	NPD4632	Approved
0.7204	Intermediate Similarity	NPD6929	Approved
0.7196	Intermediate Similarity	NPD4768	Approved
0.7196	Intermediate Similarity	NPD4767	Approved
0.7188	Intermediate Similarity	NPD4197	Approved
0.7172	Intermediate Similarity	NPD6051	Approved
0.7172	Intermediate Similarity	NPD6904	Approved
0.7172	Intermediate Similarity	NPD6673	Approved
0.7172	Intermediate Similarity	NPD6080	Approved
0.7158	Intermediate Similarity	NPD4269	Approved
0.7158	Intermediate Similarity	NPD4270	Approved
0.7157	Intermediate Similarity	NPD5210	Approved
0.7157	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6930	Phase 2
0.7128	Intermediate Similarity	NPD6931	Approved
0.7115	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD6335	Approved
0.71	Intermediate Similarity	NPD4096	Approved
0.7083	Intermediate Similarity	NPD6695	Phase 3
0.7083	Intermediate Similarity	NPD5332	Approved
0.7083	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD5331	Approved
0.708	Intermediate Similarity	NPD6274	Approved
0.7065	Intermediate Similarity	NPD6933	Approved
0.7064	Intermediate Similarity	NPD5168	Approved
0.7064	Intermediate Similarity	NPD4730	Approved
0.7064	Intermediate Similarity	NPD4729	Approved
0.7064	Intermediate Similarity	NPD5128	Approved
0.7053	Intermediate Similarity	NPD4790	Discontinued
0.7053	Intermediate Similarity	NPD4139	Approved
0.7053	Intermediate Similarity	NPD4692	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7041	Intermediate Similarity	NPD5205	Approved
0.7041	Intermediate Similarity	NPD4138	Approved
0.7041	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD4689	Approved
0.7041	Intermediate Similarity	NPD4688	Approved
0.7041	Intermediate Similarity	NPD4690	Approved
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7037	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD4687	Approved
0.703	Intermediate Similarity	NPD5693	Phase 1
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6317	Approved
0.7018	Intermediate Similarity	NPD6009	Approved
0.701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD5276	Approved
0.7	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7151	Approved
0.699	Remote Similarity	NPD5654	Approved
0.6989	Remote Similarity	NPD6925	Approved
0.6989	Remote Similarity	NPD5776	Phase 2
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6923	Approved
0.6966	Remote Similarity	NPD6922	Approved
0.6961	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD4820	Approved
0.6947	Remote Similarity	NPD4819	Approved
0.6947	Remote Similarity	NPD4748	Discontinued
0.6947	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4821	Approved
0.6947	Remote Similarity	NPD4822	Approved
0.6947	Remote Similarity	NPD4252	Approved
0.6947	Remote Similarity	NPD7514	Phase 3

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