NPASS Compound

Structure

NPC474704 OpenBabel07101719512D 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 -3.1653 -5.3212 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 3.9641 2.8660 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 2.9641 2.8660 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 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 2 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.7321 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 19 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 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 28 1 0 0 0 0 18 31 1 0 0 0 0 20 9 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 1 0 0 0 24 28 1 0 0 0 0 25 28 1 6 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	5.957
LogD:	4.151
LogS:	-4.245
# 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:	0.392
Synthetic Accessibility Score:	4.886
Fsp3:	0.833
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:	-5.321
MDCK Permeability:	7.184857167885639e-06
Pgp-inhibitor:	0.118
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.727
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	93.89244079589844%
Volume Distribution (VD):	0.6
Pgp-substrate:	2.0815188884735107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.552
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.285
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	7.478
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.678
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.415
Skin Sensitization:	0.385
Carcinogencity:	0.149
Eye Corrosion:	0.004
Eye Irritation:	0.034
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC474704

Natural Product ID:	NPC474704
*Common Name:**	3-Alpha,29-Dihydroxytirucalla-7,24-Dien-21-Oic Acid
IUPAC Name:	(2S)-2-[(3R,4S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4-(hydroxymethyl)-4,10,13,14-tetramethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	NWCRCEJGWLWBDH-NLTIPYINSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-19(2)8-7-9-20(26(33)34)21-12-16-30(6)23-10-11-24-27(3,22(23)13-17-29(21,30)5)15-14-25(32)28(24,4)18-31/h8,10,20-22,24-25,31-32H,7,9,11-18H2,1-6H3,(H,33,34)/t20-,21-,22-,24+,25+,27+,28+,29-,30+/m0/s1
SMILES:	CC(=CCCC(C1CCC2(C1(CCC3C2=CCC4C3(CCC(C4(C)CO)O)C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479702
PubChem CID:	10719252
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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]

☑ 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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	>	100.0	ug.mL-1	PMID[522499]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	26.0	%	PMID[522499]

☑ 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 NPC474704 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	1037
0.2-0.3	4572
0.3-0.4	13907
0.4-0.5	8227
0.5-0.6	5662
0.6-0.7	5100
0.7-0.8	3202
0.8-0.85	659
0.85-0.9	140
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475921
0.9759	High Similarity	NPC142361
0.9759	High Similarity	NPC474684
0.9535	High Similarity	NPC189520
0.9524	High Similarity	NPC233836
0.9524	High Similarity	NPC187376
0.9524	High Similarity	NPC159046
0.9425	High Similarity	NPC470376
0.9425	High Similarity	NPC470375
0.9419	High Similarity	NPC471896
0.9412	High Similarity	NPC242864
0.9405	High Similarity	NPC155011
0.9405	High Similarity	NPC28252
0.9405	High Similarity	NPC55309
0.931	High Similarity	NPC212301
0.931	High Similarity	NPC86266
0.931	High Similarity	NPC110657
0.9302	High Similarity	NPC77168
0.9302	High Similarity	NPC84271
0.9302	High Similarity	NPC102414
0.9205	High Similarity	NPC170220
0.9205	High Similarity	NPC107674
0.9205	High Similarity	NPC470224
0.9205	High Similarity	NPC141497
0.9195	High Similarity	NPC175628
0.9195	High Similarity	NPC111585
0.9195	High Similarity	NPC469400
0.9195	High Similarity	NPC148414
0.9176	High Similarity	NPC73038
0.9101	High Similarity	NPC469406
0.9101	High Similarity	NPC49670
0.9091	High Similarity	NPC26888
0.9091	High Similarity	NPC297265
0.9091	High Similarity	NPC23434
0.908	High Similarity	NPC234346
0.908	High Similarity	NPC293048
0.908	High Similarity	NPC270768
0.908	High Similarity	NPC31985
0.908	High Similarity	NPC263393
0.908	High Similarity	NPC61543
0.908	High Similarity	NPC59263
0.908	High Similarity	NPC225585
0.908	High Similarity	NPC121798
0.908	High Similarity	NPC130520
0.908	High Similarity	NPC474889
0.908	High Similarity	NPC128496
0.908	High Similarity	NPC1015
0.908	High Similarity	NPC127689
0.907	High Similarity	NPC264005
0.907	High Similarity	NPC96496
0.907	High Similarity	NPC269360
0.9011	High Similarity	NPC108078
0.9	High Similarity	NPC45324
0.9	High Similarity	NPC162001
0.9	High Similarity	NPC279974
0.9	High Similarity	NPC222845
0.8989	High Similarity	NPC477855
0.8977	High Similarity	NPC130278
0.8977	High Similarity	NPC470589
0.8977	High Similarity	NPC111110
0.8977	High Similarity	NPC126369
0.8966	High Similarity	NPC52169
0.8966	High Similarity	NPC182797
0.8953	High Similarity	NPC94755
0.8953	High Similarity	NPC325594
0.8953	High Similarity	NPC474970
0.8953	High Similarity	NPC2783
0.8941	High Similarity	NPC165064
0.8941	High Similarity	NPC59453
0.8941	High Similarity	NPC221758
0.8913	High Similarity	NPC119036
0.8901	High Similarity	NPC120708
0.8901	High Similarity	NPC173272
0.8901	High Similarity	NPC327788
0.8889	High Similarity	NPC159410
0.8889	High Similarity	NPC166906
0.8876	High Similarity	NPC288833
0.8876	High Similarity	NPC324341
0.8876	High Similarity	NPC966
0.8876	High Similarity	NPC228784
0.8876	High Similarity	NPC155120
0.8876	High Similarity	NPC282616
0.8876	High Similarity	NPC154101
0.8864	High Similarity	NPC213832
0.8864	High Similarity	NPC274330
0.8864	High Similarity	NPC32830
0.8864	High Similarity	NPC474245
0.8864	High Similarity	NPC290972
0.8864	High Similarity	NPC25906
0.8864	High Similarity	NPC64872
0.8864	High Similarity	NPC143232
0.8864	High Similarity	NPC57954
0.8864	High Similarity	NPC198664
0.8851	High Similarity	NPC18064
0.8851	High Similarity	NPC98442
0.8851	High Similarity	NPC88716
0.8851	High Similarity	NPC33768
0.8851	High Similarity	NPC475740
0.8851	High Similarity	NPC130577
0.8851	High Similarity	NPC68160
0.8851	High Similarity	NPC102683
0.8851	High Similarity	NPC242468
0.8851	High Similarity	NPC293564
0.8851	High Similarity	NPC51700
0.8851	High Similarity	NPC90652
0.8851	High Similarity	NPC142415
0.8851	High Similarity	NPC307426
0.8851	High Similarity	NPC171203
0.8837	High Similarity	NPC470574
0.8837	High Similarity	NPC294438
0.8837	High Similarity	NPC264317
0.881	High Similarity	NPC147066
0.881	High Similarity	NPC473420
0.8791	High Similarity	NPC317586
0.8791	High Similarity	NPC469599
0.8791	High Similarity	NPC470016
0.8791	High Similarity	NPC69548
0.8791	High Similarity	NPC88310
0.8791	High Similarity	NPC48330
0.8791	High Similarity	NPC184848
0.8778	High Similarity	NPC229281
0.8778	High Similarity	NPC86368
0.8778	High Similarity	NPC475255
0.8764	High Similarity	NPC227467
0.8764	High Similarity	NPC290614
0.8764	High Similarity	NPC291028
0.8764	High Similarity	NPC86372
0.8764	High Similarity	NPC273621
0.8764	High Similarity	NPC210037
0.8764	High Similarity	NPC120968
0.8764	High Similarity	NPC172361
0.8764	High Similarity	NPC18872
0.8764	High Similarity	NPC477872
0.8764	High Similarity	NPC7260
0.875	High Similarity	NPC16377
0.875	High Similarity	NPC471722
0.875	High Similarity	NPC17733
0.875	High Similarity	NPC193360
0.875	High Similarity	NPC328539
0.875	High Similarity	NPC471900
0.875	High Similarity	NPC246708
0.875	High Similarity	NPC474719
0.875	High Similarity	NPC146937
0.875	High Similarity	NPC473242
0.875	High Similarity	NPC470417
0.875	High Similarity	NPC290690
0.875	High Similarity	NPC181225
0.875	High Similarity	NPC40552
0.875	High Similarity	NPC474512
0.875	High Similarity	NPC470629
0.8736	High Similarity	NPC72133
0.8736	High Similarity	NPC474732
0.8736	High Similarity	NPC474778
0.8736	High Similarity	NPC474733
0.8736	High Similarity	NPC31564
0.8736	High Similarity	NPC51014
0.8736	High Similarity	NPC12774
0.8736	High Similarity	NPC72638
0.8736	High Similarity	NPC145879
0.8721	High Similarity	NPC214043
0.8721	High Similarity	NPC85774
0.8721	High Similarity	NPC82902
0.871	High Similarity	NPC477854
0.871	High Similarity	NPC477813
0.871	High Similarity	NPC186810
0.871	High Similarity	NPC48647
0.871	High Similarity	NPC114274
0.8706	High Similarity	NPC151519
0.8696	High Similarity	NPC471153
0.8696	High Similarity	NPC305483
0.8696	High Similarity	NPC477853
0.8696	High Similarity	NPC328162
0.8696	High Similarity	NPC96859
0.8681	High Similarity	NPC282395
0.8681	High Similarity	NPC299996
0.8681	High Similarity	NPC20235
0.8681	High Similarity	NPC80365
0.8681	High Similarity	NPC159365
0.8681	High Similarity	NPC114159
0.8681	High Similarity	NPC111015
0.8681	High Similarity	NPC6818
0.8681	High Similarity	NPC88116
0.8681	High Similarity	NPC32407
0.8681	High Similarity	NPC191412
0.8681	High Similarity	NPC222047
0.8681	High Similarity	NPC231063
0.8681	High Similarity	NPC145667
0.8681	High Similarity	NPC196485
0.8681	High Similarity	NPC245972
0.8681	High Similarity	NPC263548
0.8667	High Similarity	NPC105189
0.8667	High Similarity	NPC71074
0.8667	High Similarity	NPC475708
0.8667	High Similarity	NPC65120
0.8667	High Similarity	NPC187722
0.8667	High Similarity	NPC474525
0.8667	High Similarity	NPC235884
0.8667	High Similarity	NPC473998
0.8667	High Similarity	NPC158030
0.8667	High Similarity	NPC472149

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 NPC474704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1347
0.2-0.3	3952
0.3-0.4	2490
0.4-0.5	674
0.5-0.6	202
0.6-0.7	117
0.7-0.8	147
0.8-0.85	64
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8941	High Similarity	NPD4786	Approved
0.8864	High Similarity	NPD5328	Approved
0.8837	High Similarity	NPD7520	Clinical (unspecified phase)
0.8778	High Similarity	NPD6399	Phase 3
0.8736	High Similarity	NPD3618	Phase 1
0.8706	High Similarity	NPD3667	Approved
0.8667	High Similarity	NPD6079	Approved
0.8667	High Similarity	NPD7515	Phase 2
0.8557	High Similarity	NPD7128	Approved
0.8557	High Similarity	NPD6675	Approved
0.8557	High Similarity	NPD6402	Approved
0.8557	High Similarity	NPD5739	Approved
0.8404	Intermediate Similarity	NPD4755	Approved
0.8404	Intermediate Similarity	NPD6084	Phase 2
0.8404	Intermediate Similarity	NPD6083	Phase 2
0.8384	Intermediate Similarity	NPD7320	Approved
0.8384	Intermediate Similarity	NPD6899	Approved
0.8384	Intermediate Similarity	NPD6881	Approved
0.837	Intermediate Similarity	NPD4202	Approved
0.83	Intermediate Similarity	NPD6373	Approved
0.83	Intermediate Similarity	NPD6372	Approved
0.8298	Intermediate Similarity	NPD4697	Phase 3
0.8298	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD5221	Approved
0.8298	Intermediate Similarity	NPD5222	Approved
0.8295	Intermediate Similarity	NPD3133	Approved
0.8295	Intermediate Similarity	NPD3666	Approved
0.8295	Intermediate Similarity	NPD3665	Phase 1
0.8283	Intermediate Similarity	NPD5697	Approved
0.8283	Intermediate Similarity	NPD5701	Approved
0.828	Intermediate Similarity	NPD7748	Approved
0.8261	Intermediate Similarity	NPD8035	Phase 2
0.8261	Intermediate Similarity	NPD8034	Phase 2
0.8256	Intermediate Similarity	NPD7525	Registered
0.8242	Intermediate Similarity	NPD4753	Phase 2
0.8229	Intermediate Similarity	NPD5286	Approved
0.8229	Intermediate Similarity	NPD4700	Approved
0.8229	Intermediate Similarity	NPD4696	Approved
0.8229	Intermediate Similarity	NPD5285	Approved
0.8218	Intermediate Similarity	NPD6883	Approved
0.8218	Intermediate Similarity	NPD7102	Approved
0.8218	Intermediate Similarity	NPD7290	Approved
0.8214	Intermediate Similarity	NPD6117	Approved
0.8211	Intermediate Similarity	NPD5173	Approved
0.8137	Intermediate Similarity	NPD8130	Phase 1
0.8137	Intermediate Similarity	NPD6869	Approved
0.8137	Intermediate Similarity	NPD6649	Approved
0.8137	Intermediate Similarity	NPD6847	Approved
0.8137	Intermediate Similarity	NPD6617	Approved
0.8137	Intermediate Similarity	NPD6650	Approved
0.8132	Intermediate Similarity	NPD6672	Approved
0.8132	Intermediate Similarity	NPD5737	Approved
0.8125	Intermediate Similarity	NPD7638	Approved
0.8119	Intermediate Similarity	NPD6013	Approved
0.8119	Intermediate Similarity	NPD6012	Approved
0.8119	Intermediate Similarity	NPD6014	Approved
0.8118	Intermediate Similarity	NPD6116	Phase 1
0.8111	Intermediate Similarity	NPD7334	Approved
0.8111	Intermediate Similarity	NPD6684	Approved
0.8111	Intermediate Similarity	NPD7521	Approved
0.8111	Intermediate Similarity	NPD6409	Approved
0.8111	Intermediate Similarity	NPD7146	Approved
0.8111	Intermediate Similarity	NPD5330	Approved
0.8095	Intermediate Similarity	NPD7339	Approved
0.8095	Intermediate Similarity	NPD6942	Approved
0.809	Intermediate Similarity	NPD3668	Phase 3
0.8061	Intermediate Similarity	NPD5224	Approved
0.8061	Intermediate Similarity	NPD5225	Approved
0.8061	Intermediate Similarity	NPD4633	Approved
0.8061	Intermediate Similarity	NPD5211	Phase 2
0.8061	Intermediate Similarity	NPD5226	Approved
0.8058	Intermediate Similarity	NPD8297	Approved
0.8058	Intermediate Similarity	NPD6882	Approved
0.8041	Intermediate Similarity	NPD7640	Approved
0.8041	Intermediate Similarity	NPD7639	Approved
0.8023	Intermediate Similarity	NPD6118	Approved
0.8023	Intermediate Similarity	NPD6115	Approved
0.8023	Intermediate Similarity	NPD6697	Approved
0.8023	Intermediate Similarity	NPD6114	Approved
0.8021	Intermediate Similarity	NPD7902	Approved
0.802	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD5695	Phase 3
0.798	Intermediate Similarity	NPD5174	Approved
0.798	Intermediate Similarity	NPD5175	Approved
0.7976	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5223	Approved
0.7938	Intermediate Similarity	NPD5696	Approved
0.7935	Intermediate Similarity	NPD6903	Approved
0.7935	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD5279	Phase 3
0.79	Intermediate Similarity	NPD5141	Approved
0.7865	Intermediate Similarity	NPD4223	Phase 3
0.7865	Intermediate Similarity	NPD4221	Approved
0.7822	Intermediate Similarity	NPD4768	Approved
0.7822	Intermediate Similarity	NPD4767	Approved
0.7812	Intermediate Similarity	NPD5210	Approved
0.7812	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4629	Approved
0.7802	Intermediate Similarity	NPD5329	Approved
0.78	Intermediate Similarity	NPD4754	Approved
0.7791	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD7645	Phase 2
0.7717	Intermediate Similarity	NPD6098	Approved
0.7717	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD4197	Approved
0.7684	Intermediate Similarity	NPD5284	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.7684	Intermediate Similarity	NPD5281	Approved
0.767	Intermediate Similarity	NPD4729	Approved
0.767	Intermediate Similarity	NPD5128	Approved
0.767	Intermediate Similarity	NPD4730	Approved
0.7664	Intermediate Similarity	NPD6868	Approved
0.7664	Intermediate Similarity	NPD6274	Approved
0.766	Intermediate Similarity	NPD6904	Approved
0.766	Intermediate Similarity	NPD6673	Approved
0.766	Intermediate Similarity	NPD6080	Approved
0.7642	Intermediate Similarity	NPD4632	Approved
0.7615	Intermediate Similarity	NPD7100	Approved
0.7615	Intermediate Similarity	NPD7101	Approved
0.7614	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4788	Approved
0.7529	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5205	Approved
0.7527	Intermediate Similarity	NPD4689	Approved
0.7527	Intermediate Similarity	NPD4690	Approved
0.7527	Intermediate Similarity	NPD4688	Approved
0.7527	Intermediate Similarity	NPD4693	Phase 3
0.7527	Intermediate Similarity	NPD4138	Approved
0.7524	Intermediate Similarity	NPD4634	Approved
0.7524	Intermediate Similarity	NPD5249	Phase 3
0.7524	Intermediate Similarity	NPD5251	Approved
0.7524	Intermediate Similarity	NPD5247	Approved
0.7524	Intermediate Similarity	NPD5248	Approved
0.7524	Intermediate Similarity	NPD5250	Approved
0.7523	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5168	Approved
0.7477	Intermediate Similarity	NPD6908	Approved
0.7477	Intermediate Similarity	NPD6909	Approved
0.7476	Intermediate Similarity	NPD6008	Approved
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5215	Approved
0.7453	Intermediate Similarity	NPD5217	Approved
0.7453	Intermediate Similarity	NPD5216	Approved
0.7431	Intermediate Similarity	NPD6009	Approved
0.7431	Intermediate Similarity	NPD6317	Approved
0.7416	Intermediate Similarity	NPD3617	Approved
0.7404	Intermediate Similarity	NPD6412	Phase 2
0.7387	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD5208	Approved
0.7364	Intermediate Similarity	NPD6313	Approved
0.7364	Intermediate Similarity	NPD6314	Approved
0.7358	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5135	Approved
0.7358	Intermediate Similarity	NPD5169	Approved
0.7356	Intermediate Similarity	NPD6926	Approved
0.7356	Intermediate Similarity	NPD6924	Approved
0.7353	Intermediate Similarity	NPD7632	Discontinued
0.7347	Intermediate Similarity	NPD6001	Approved
0.734	Intermediate Similarity	NPD5690	Phase 2
0.734	Intermediate Similarity	NPD5280	Approved
0.734	Intermediate Similarity	NPD4694	Approved
0.7326	Intermediate Similarity	NPD4243	Approved
0.732	Intermediate Similarity	NPD5693	Phase 1
0.732	Intermediate Similarity	NPD7637	Suspended
0.732	Intermediate Similarity	NPD6050	Approved
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6051	Approved
0.729	Intermediate Similarity	NPD5127	Approved
0.7281	Intermediate Similarity	NPD7492	Approved
0.7263	Intermediate Similarity	NPD3573	Approved
0.7253	Intermediate Similarity	NPD5368	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7232	Intermediate Similarity	NPD6054	Approved
0.7232	Intermediate Similarity	NPD6059	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7217	Intermediate Similarity	NPD6616	Approved
0.7216	Intermediate Similarity	NPD5692	Phase 3
0.7209	Intermediate Similarity	NPD4747	Approved
0.7204	Intermediate Similarity	NPD5362	Discontinued
0.7193	Intermediate Similarity	NPD7604	Phase 2
0.7191	Intermediate Similarity	NPD6933	Approved
0.7174	Intermediate Similarity	NPD4139	Approved
0.7174	Intermediate Similarity	NPD4692	Approved
0.7168	Intermediate Similarity	NPD5983	Phase 2
0.7168	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4784	Approved
0.7159	Intermediate Similarity	NPD4785	Approved
0.7155	Intermediate Similarity	NPD7078	Approved
0.7155	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD6929	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD5694	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