NPASS Compound

Structure

CID275740 OpenBabel06191716082D 32 35 0 0 1 0 0 0 0 0999 V2000 1.8172 -5.8003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2757 -4.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3578 -3.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3725 2.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 -0.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3027 -3.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -4.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8162 -2.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 -0.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2143 0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3717 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 -1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6850 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6867 1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3032 -4.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8435 -1.4594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6861 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5296 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2146 1.4590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3723 1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5294 0.4860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9729 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 0.0224 1.9602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0808 1.9586 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 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 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 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 20 3 1 6 0 0 0 20 21 1 0 0 0 0 21 29 1 1 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 30 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	7.63
LogD:	5.165
LogS:	-5.495
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	4.683
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	1.3904246770835016e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	92.09503936767578%
Volume Distribution (VD):	0.995
Pgp-substrate:	2.1381776332855225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.24
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	22.485
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.94
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.919
Carcinogencity:	0.362
Eye Corrosion:	0.017
Eye Irritation:	0.016
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC275740

Natural Product ID:	NPC275740
*Common Name:**	Tirucalla-8,24-Diene-3Beta-Ol-7-One
IUPAC Name:	(3S,5R,10S,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methylhept-5-en-2-yl]-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms:	epi-kansenone
Standard InCHIKey:	TVMGQCAMNPECHD-VGYIVZNUSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)10-9-11-20(3)21-12-17-30(8)26-22(13-16-29(21,30)7)28(6)15-14-25(32)27(4,5)24(28)18-23(26)31/h10,20-21,24-25,32H,9,11-18H2,1-8H3/t20-,21-,24-,25-,28+,29-,30+/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@@H]1CC[C@]2(C)C3=C(CC[C@@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513851
PubChem CID:	21629616
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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT693	Organism	Xenopus laevis	Xenopus laevis	Activity	>	50.0	%	PMID[566549]

☑ 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 NPC275740 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	162
0.1-0.2	1163
0.2-0.3	5251
0.3-0.4	13256
0.4-0.5	9407
0.5-0.6	6543
0.6-0.7	4681
0.7-0.8	1778
0.8-0.85	305
0.85-0.9	112
0.9-0.95	26
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86319
0.988	High Similarity	NPC131470
0.988	High Similarity	NPC143767
0.9651	High Similarity	NPC69454
0.9647	High Similarity	NPC183283
0.9643	High Similarity	NPC471722
0.9643	High Similarity	NPC328539
0.9639	High Similarity	NPC72133
0.9535	High Similarity	NPC63748
0.9432	High Similarity	NPC259286
0.9419	High Similarity	NPC191684
0.9398	High Similarity	NPC473246
0.9326	High Similarity	NPC249954
0.9318	High Similarity	NPC166906
0.931	High Similarity	NPC168027
0.931	High Similarity	NPC185936
0.9294	High Similarity	NPC475740
0.9286	High Similarity	NPC470574
0.9213	High Similarity	NPC317586
0.9213	High Similarity	NPC470016
0.9205	High Similarity	NPC472930
0.9186	High Similarity	NPC471724
0.9176	High Similarity	NPC475022
0.9176	High Similarity	NPC474732
0.9176	High Similarity	NPC474733
0.9176	High Similarity	NPC94755
0.9176	High Similarity	NPC118648
0.9176	High Similarity	NPC31564
0.9176	High Similarity	NPC222613
0.9176	High Similarity	NPC145879
0.9176	High Similarity	NPC474778
0.9167	High Similarity	NPC85774
0.9167	High Similarity	NPC214043
0.9111	High Similarity	NPC305483
0.9111	High Similarity	NPC96859
0.9111	High Similarity	NPC328162
0.9091	High Similarity	NPC272746
0.9091	High Similarity	NPC233116
0.908	High Similarity	NPC473999
0.908	High Similarity	NPC31985
0.908	High Similarity	NPC309603
0.908	High Similarity	NPC186688
0.908	High Similarity	NPC1015
0.907	High Similarity	NPC187376
0.907	High Similarity	NPC58063
0.907	High Similarity	NPC233836
0.907	High Similarity	NPC159046
0.9059	High Similarity	NPC469948
0.9048	High Similarity	NPC278648
0.9048	High Similarity	NPC476082
0.8989	High Similarity	NPC475255
0.8977	High Similarity	NPC48010
0.8977	High Similarity	NPC85173
0.8977	High Similarity	NPC126993
0.8966	High Similarity	NPC53911
0.8953	High Similarity	NPC28252
0.8953	High Similarity	NPC55309
0.8941	High Similarity	NPC59453
0.8941	High Similarity	NPC221758
0.8901	High Similarity	NPC192428
0.8889	High Similarity	NPC245972
0.8889	High Similarity	NPC196485
0.8889	High Similarity	NPC111015
0.8876	High Similarity	NPC473998
0.8876	High Similarity	NPC475806
0.8864	High Similarity	NPC26959
0.8864	High Similarity	NPC77168
0.8864	High Similarity	NPC84271
0.8864	High Similarity	NPC477943
0.8864	High Similarity	NPC102414
0.8864	High Similarity	NPC119416
0.8864	High Similarity	NPC268406
0.8851	High Similarity	NPC142361
0.8851	High Similarity	NPC136548
0.8851	High Similarity	NPC141292
0.8851	High Similarity	NPC474684
0.8837	High Similarity	NPC202868
0.8837	High Similarity	NPC474083
0.883	High Similarity	NPC473424
0.8824	High Similarity	NPC64600
0.8817	High Similarity	NPC316964
0.8804	High Similarity	NPC18509
0.8804	High Similarity	NPC43747
0.8791	High Similarity	NPC173875
0.8791	High Similarity	NPC255809
0.8791	High Similarity	NPC318282
0.8791	High Similarity	NPC473170
0.8791	High Similarity	NPC469995
0.8791	High Similarity	NPC174948
0.8791	High Similarity	NPC472932
0.8791	High Similarity	NPC200702
0.8791	High Similarity	NPC271195
0.8778	High Similarity	NPC134826
0.8778	High Similarity	NPC12722
0.875	High Similarity	NPC193360
0.875	High Similarity	NPC242864
0.875	High Similarity	NPC292491
0.875	High Similarity	NPC310752
0.8736	High Similarity	NPC51014
0.8736	High Similarity	NPC327115
0.8721	High Similarity	NPC58841
0.8721	High Similarity	NPC237712
0.8721	High Similarity	NPC321187
0.8721	High Similarity	NPC161423
0.8721	High Similarity	NPC82902
0.8721	High Similarity	NPC227064
0.8721	High Similarity	NPC329043
0.8721	High Similarity	NPC472265
0.871	High Similarity	NPC114274
0.8706	High Similarity	NPC151519
0.8696	High Similarity	NPC173272
0.8696	High Similarity	NPC95565
0.8696	High Similarity	NPC328371
0.869	High Similarity	NPC164999
0.8681	High Similarity	NPC8993
0.8681	High Similarity	NPC471207
0.8667	High Similarity	NPC297265
0.8667	High Similarity	NPC19114
0.8652	High Similarity	NPC32830
0.8652	High Similarity	NPC472973
0.8652	High Similarity	NPC474704
0.8652	High Similarity	NPC474245
0.8652	High Similarity	NPC475921
0.8652	High Similarity	NPC123912
0.8636	High Similarity	NPC138756
0.8636	High Similarity	NPC475772
0.8636	High Similarity	NPC93778
0.8632	High Similarity	NPC477915
0.8621	High Similarity	NPC197823
0.8621	High Similarity	NPC471224
0.8621	High Similarity	NPC474218
0.8617	High Similarity	NPC287833
0.8617	High Similarity	NPC51370
0.8617	High Similarity	NPC144956
0.8617	High Similarity	NPC112167
0.8602	High Similarity	NPC108078
0.8602	High Similarity	NPC320306
0.8602	High Similarity	NPC190554
0.8587	High Similarity	NPC48330
0.8587	High Similarity	NPC127063
0.8571	High Similarity	NPC250575
0.8571	High Similarity	NPC472490
0.8571	High Similarity	NPC477855
0.8556	High Similarity	NPC175628
0.8556	High Similarity	NPC129913
0.8556	High Similarity	NPC20388
0.8556	High Similarity	NPC136801
0.8556	High Similarity	NPC469400
0.8556	High Similarity	NPC148414
0.8556	High Similarity	NPC111585
0.8554	High Similarity	NPC214570
0.8554	High Similarity	NPC197659
0.8539	High Similarity	NPC474677
0.8539	High Similarity	NPC158778
0.8539	High Similarity	NPC472802
0.8539	High Similarity	NPC474925
0.8539	High Similarity	NPC328313
0.8526	High Similarity	NPC163372
0.8526	High Similarity	NPC472924
0.8526	High Similarity	NPC302537
0.8523	High Similarity	NPC469994
0.8523	High Similarity	NPC155011
0.8523	High Similarity	NPC89077
0.8523	High Similarity	NPC20688
0.8523	High Similarity	NPC158393
0.8511	High Similarity	NPC147954
0.8511	High Similarity	NPC471717
0.8511	High Similarity	NPC197386
0.8511	High Similarity	NPC103051
0.8506	High Similarity	NPC146683
0.8506	High Similarity	NPC33913
0.8495	Intermediate Similarity	NPC472941
0.8495	Intermediate Similarity	NPC117133
0.8495	Intermediate Similarity	NPC456
0.8488	Intermediate Similarity	NPC48362
0.8478	Intermediate Similarity	NPC469406
0.8478	Intermediate Similarity	NPC184870
0.8471	Intermediate Similarity	NPC472478
0.8471	Intermediate Similarity	NPC2482
0.8469	Intermediate Similarity	NPC472925
0.8462	Intermediate Similarity	NPC212301
0.8462	Intermediate Similarity	NPC472978
0.8462	Intermediate Similarity	NPC131872
0.8462	Intermediate Similarity	NPC86266
0.8462	Intermediate Similarity	NPC155304
0.8462	Intermediate Similarity	NPC110657
0.8462	Intermediate Similarity	NPC23434
0.8462	Intermediate Similarity	NPC99380
0.8462	Intermediate Similarity	NPC472975
0.8462	Intermediate Similarity	NPC189520
0.8462	Intermediate Similarity	NPC26888
0.8454	Intermediate Similarity	NPC209502
0.8454	Intermediate Similarity	NPC204833
0.8452	Intermediate Similarity	NPC275910
0.8444	Intermediate Similarity	NPC214387
0.8444	Intermediate Similarity	NPC69627
0.8444	Intermediate Similarity	NPC76879
0.8444	Intermediate Similarity	NPC474889
0.8444	Intermediate Similarity	NPC472971
0.8444	Intermediate Similarity	NPC472970

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 NPC275740 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	1522
0.2-0.3	4170
0.3-0.4	2312
0.4-0.5	536
0.5-0.6	165
0.6-0.7	129
0.7-0.8	131
0.8-0.85	25
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9762	High Similarity	NPD5328	Approved
0.9535	High Similarity	NPD6079	Approved
0.9176	High Similarity	NPD3618	Phase 1
0.8941	High Similarity	NPD4786	Approved
0.8901	High Similarity	NPD4697	Phase 3
0.8901	High Similarity	NPD5222	Approved
0.8901	High Similarity	NPD5220	Clinical (unspecified phase)
0.8901	High Similarity	NPD5221	Approved
0.8804	High Similarity	NPD5173	Approved
0.8804	High Similarity	NPD4755	Approved
0.8778	High Similarity	NPD4202	Approved
0.8736	High Similarity	NPD5279	Phase 3
0.8721	High Similarity	NPD3666	Approved
0.8721	High Similarity	NPD3665	Phase 1
0.8721	High Similarity	NPD3133	Approved
0.8706	High Similarity	NPD3667	Approved
0.8617	High Similarity	NPD5286	Approved
0.8617	High Similarity	NPD5285	Approved
0.8617	High Similarity	NPD4700	Approved
0.8617	High Similarity	NPD4696	Approved
0.8526	High Similarity	NPD5223	Approved
0.8438	Intermediate Similarity	NPD5226	Approved
0.8438	Intermediate Similarity	NPD5224	Approved
0.8438	Intermediate Similarity	NPD5225	Approved
0.8438	Intermediate Similarity	NPD5211	Phase 2
0.8438	Intermediate Similarity	NPD4633	Approved
0.8367	Intermediate Similarity	NPD6675	Approved
0.8367	Intermediate Similarity	NPD5739	Approved
0.8367	Intermediate Similarity	NPD7128	Approved
0.8367	Intermediate Similarity	NPD6402	Approved
0.8351	Intermediate Similarity	NPD5175	Approved
0.8351	Intermediate Similarity	NPD5174	Approved
0.8351	Intermediate Similarity	NPD4754	Approved
0.8276	Intermediate Similarity	NPD4221	Approved
0.8276	Intermediate Similarity	NPD4223	Phase 3
0.8265	Intermediate Similarity	NPD5141	Approved
0.8261	Intermediate Similarity	NPD7515	Phase 2
0.8242	Intermediate Similarity	NPD4753	Phase 2
0.8202	Intermediate Similarity	NPD5329	Approved
0.82	Intermediate Similarity	NPD6899	Approved
0.82	Intermediate Similarity	NPD7320	Approved
0.82	Intermediate Similarity	NPD6881	Approved
0.8182	Intermediate Similarity	NPD4767	Approved
0.8182	Intermediate Similarity	NPD4768	Approved
0.8119	Intermediate Similarity	NPD6372	Approved
0.8119	Intermediate Similarity	NPD6373	Approved
0.8111	Intermediate Similarity	NPD5280	Approved
0.8111	Intermediate Similarity	NPD4694	Approved
0.8111	Intermediate Similarity	NPD5690	Phase 2
0.81	Intermediate Similarity	NPD5697	Approved
0.81	Intermediate Similarity	NPD5701	Approved
0.809	Intermediate Similarity	NPD4197	Approved
0.8039	Intermediate Similarity	NPD7102	Approved
0.8039	Intermediate Similarity	NPD7290	Approved
0.8039	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD5128	Approved
0.802	Intermediate Similarity	NPD4730	Approved
0.802	Intermediate Similarity	NPD6011	Approved
0.802	Intermediate Similarity	NPD4729	Approved
0.802	Intermediate Similarity	NPD5168	Approved
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD6399	Phase 3
0.7961	Intermediate Similarity	NPD8130	Phase 1
0.7961	Intermediate Similarity	NPD6617	Approved
0.7961	Intermediate Similarity	NPD6869	Approved
0.7961	Intermediate Similarity	NPD6649	Approved
0.7961	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6847	Approved
0.7961	Intermediate Similarity	NPD6650	Approved
0.7941	Intermediate Similarity	NPD6012	Approved
0.7941	Intermediate Similarity	NPD6014	Approved
0.7941	Intermediate Similarity	NPD6013	Approved
0.7912	Intermediate Similarity	NPD5205	Approved
0.7912	Intermediate Similarity	NPD4688	Approved
0.7912	Intermediate Similarity	NPD5330	Approved
0.7912	Intermediate Similarity	NPD6409	Approved
0.7912	Intermediate Similarity	NPD7146	Approved
0.7912	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6684	Approved
0.7912	Intermediate Similarity	NPD4689	Approved
0.7912	Intermediate Similarity	NPD4693	Phase 3
0.7912	Intermediate Similarity	NPD7334	Approved
0.7912	Intermediate Similarity	NPD7521	Approved
0.7912	Intermediate Similarity	NPD4138	Approved
0.7912	Intermediate Similarity	NPD4690	Approved
0.7895	Intermediate Similarity	NPD7748	Approved
0.7889	Intermediate Similarity	NPD3668	Phase 3
0.7885	Intermediate Similarity	NPD8297	Approved
0.7885	Intermediate Similarity	NPD6882	Approved
0.7882	Intermediate Similarity	NPD7339	Approved
0.7882	Intermediate Similarity	NPD6942	Approved
0.7864	Intermediate Similarity	NPD5247	Approved
0.7864	Intermediate Similarity	NPD5135	Approved
0.7864	Intermediate Similarity	NPD5248	Approved
0.7864	Intermediate Similarity	NPD5169	Approved
0.7864	Intermediate Similarity	NPD5249	Phase 3
0.7864	Intermediate Similarity	NPD4634	Approved
0.7864	Intermediate Similarity	NPD5250	Approved
0.7864	Intermediate Similarity	NPD5251	Approved
0.7864	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7525	Registered
0.7835	Intermediate Similarity	NPD6084	Phase 2
0.7835	Intermediate Similarity	NPD6083	Phase 2
0.7816	Intermediate Similarity	NPD3617	Approved
0.7812	Intermediate Similarity	NPD5210	Approved
0.7812	Intermediate Similarity	NPD5695	Phase 3
0.7812	Intermediate Similarity	NPD4629	Approved
0.7788	Intermediate Similarity	NPD5127	Approved
0.7788	Intermediate Similarity	NPD5216	Approved
0.7788	Intermediate Similarity	NPD5217	Approved
0.7788	Intermediate Similarity	NPD5215	Approved
0.7778	Intermediate Similarity	NPD4788	Approved
0.7765	Intermediate Similarity	NPD5733	Approved
0.7742	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD6672	Approved
0.7742	Intermediate Similarity	NPD5737	Approved
0.7742	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5284	Approved
0.7684	Intermediate Similarity	NPD5281	Approved
0.7664	Intermediate Similarity	NPD6868	Approved
0.7653	Intermediate Similarity	NPD7902	Approved
0.7642	Intermediate Similarity	NPD4632	Approved
0.7619	Intermediate Similarity	NPD4747	Approved
0.7586	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4096	Approved
0.7576	Intermediate Similarity	NPD7638	Approved
0.757	Intermediate Similarity	NPD5167	Approved
0.7558	Intermediate Similarity	NPD4687	Approved
0.7556	Intermediate Similarity	NPD4139	Approved
0.7556	Intermediate Similarity	NPD4692	Approved
0.7529	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5276	Approved
0.7529	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4195	Approved
0.7523	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD4137	Phase 3
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD6008	Approved
0.7471	Intermediate Similarity	NPD3703	Phase 2
0.7455	Intermediate Similarity	NPD7101	Approved
0.7455	Intermediate Similarity	NPD7100	Approved
0.7449	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3573	Approved
0.7444	Intermediate Similarity	NPD4695	Discontinued
0.7431	Intermediate Similarity	NPD6317	Approved
0.7431	Intermediate Similarity	NPD6009	Approved
0.7423	Intermediate Similarity	NPD5133	Approved
0.7412	Intermediate Similarity	NPD4691	Approved
0.74	Intermediate Similarity	NPD5696	Approved
0.7387	Intermediate Similarity	NPD6054	Approved
0.7387	Intermediate Similarity	NPD6059	Approved
0.7368	Intermediate Similarity	NPD4518	Approved
0.7364	Intermediate Similarity	NPD6313	Approved
0.7364	Intermediate Similarity	NPD6314	Approved
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4519	Discontinued
0.734	Intermediate Similarity	NPD4623	Approved
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7321	Intermediate Similarity	NPD6908	Approved
0.7321	Intermediate Similarity	NPD6909	Approved
0.732	Intermediate Similarity	NPD8035	Phase 2
0.732	Intermediate Similarity	NPD8034	Phase 2
0.732	Intermediate Similarity	NPD6050	Approved
0.732	Intermediate Similarity	NPD6411	Approved
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD6370	Approved
0.7253	Intermediate Similarity	NPD4748	Discontinued
0.7253	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6412	Phase 2
0.7232	Intermediate Similarity	NPD6319	Approved
0.7228	Intermediate Similarity	NPD5290	Discontinued
0.7216	Intermediate Similarity	NPD5207	Approved
0.7216	Intermediate Similarity	NPD5692	Phase 3
0.7193	Intermediate Similarity	NPD7604	Phase 2
0.7191	Intermediate Similarity	NPD6117	Approved
0.7188	Intermediate Similarity	NPD5208	Approved
0.7172	Intermediate Similarity	NPD6001	Approved
0.7168	Intermediate Similarity	NPD5983	Phase 2
0.7168	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6015	Approved
0.7168	Intermediate Similarity	NPD6016	Approved
0.7159	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4058	Approved
0.7159	Intermediate Similarity	NPD6926	Approved
0.7159	Intermediate Similarity	NPD6924	Approved
0.7158	Intermediate Similarity	NPD6098	Approved
0.7143	Intermediate Similarity	NPD7331	Phase 2
0.7143	Intermediate Similarity	NPD5694	Approved
0.713	Intermediate Similarity	NPD7492	Approved
0.7126	Intermediate Similarity	NPD4243	Approved
0.7113	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7285	Clinical (unspecified phase)

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