NPASS Compound

Structure

CID259286 OpenBabel06191716062D 33 36 0 0 1 0 0 0 0 0999 V2000 0.0017 -2.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0179 -6.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5043 -5.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2494 2.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5311 -0.5232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 -3.8934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 -2.9202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6866 -0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6872 -0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2177 0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5307 -4.3798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3744 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8433 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6863 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6881 1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 -2.4338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8442 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6875 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5317 1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2180 1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8439 0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5310 -5.3531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3750 1.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5314 0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9737 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 0.0217 1.9614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0843 1.9598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6883 -5.8399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 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 14 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 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 22 1 0 0 0 0 18 23 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 1 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 32 1 6 0 0 0 25 30 1 0 0 0 0 26 33 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:	456.36
Volume:	511.671
LogP:	6.001
LogD:	4.62
LogS:	-4.681
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	4.9
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.885
MDCK Permeability:	1.7127578757936135e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.665
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154
Plasma Protein Binding (PPB):	94.0126953125%
Volume Distribution (VD):	0.82
Pgp-substrate:	3.8995277881622314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.177
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.899

ADMET: Excretion

Clearance (CL):	10.132
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.561
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.816
Carcinogencity:	0.444
Eye Corrosion:	0.006
Eye Irritation:	0.012
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC259286

Natural Product ID:	NPC259286
*Common Name:**	Kansenonol
IUPAC Name:	(3S,5R,10S,13S,14S,17S)-3-hydroxy-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms:	kansenonol
Standard InCHIKey:	HGMDURCSONKDEI-DEYHTPJLSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(10-9-14-26(2,3)33)20-11-17-30(8)25-21(12-16-29(20,30)7)28(6)15-13-24(32)27(4,5)23(28)18-22(25)31/h9,14,19-20,23-24,32-33H,10-13,15-18H2,1-8H3/b14-9+/t19-,20+,23+,24+,28-,29+,30-/m1/s1
SMILES:	C[C@H](C/C=C/C(C)(C)O)[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469076
PubChem CID:	21629617
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[495357]

☑ 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 NPC259286 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	161
0.1-0.2	1068
0.2-0.3	4421
0.3-0.4	11156
0.4-0.5	11580
0.5-0.6	7120
0.6-0.7	5018
0.7-0.8	1776
0.8-0.85	281
0.85-0.9	91
0.9-0.95	18
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC249954
0.9773	High Similarity	NPC69454
0.9659	High Similarity	NPC63748
0.9438	High Similarity	NPC475806
0.9432	High Similarity	NPC275740
0.9432	High Similarity	NPC86319
0.9333	High Similarity	NPC472930
0.9318	High Similarity	NPC143767
0.9318	High Similarity	NPC131470
0.9231	High Similarity	NPC8993
0.9222	High Similarity	NPC233116
0.9213	High Similarity	NPC473999
0.9213	High Similarity	NPC309603
0.9158	High Similarity	NPC473424
0.913	High Similarity	NPC271195
0.9111	High Similarity	NPC183283
0.9111	High Similarity	NPC48010
0.9101	High Similarity	NPC328539
0.9101	High Similarity	NPC471722
0.9091	High Similarity	NPC72133
0.9011	High Similarity	NPC473998
0.9	High Similarity	NPC472973
0.8977	High Similarity	NPC474083
0.8958	High Similarity	NPC477915
0.8936	High Similarity	NPC161147
0.8925	High Similarity	NPC318282
0.8925	High Similarity	NPC173875
0.8925	High Similarity	NPC469995
0.8925	High Similarity	NPC174948
0.8925	High Similarity	NPC472932
0.8901	High Similarity	NPC191684
0.8876	High Similarity	NPC222613
0.8876	High Similarity	NPC118648
0.8876	High Similarity	NPC475022
0.8864	High Similarity	NPC473246
0.8854	High Similarity	NPC302537
0.8854	High Similarity	NPC163372
0.8842	High Similarity	NPC103051
0.883	High Similarity	NPC328371
0.8817	High Similarity	NPC166906
0.8817	High Similarity	NPC299100
0.8804	High Similarity	NPC185936
0.8804	High Similarity	NPC472978
0.8804	High Similarity	NPC272746
0.8804	High Similarity	NPC168027
0.8791	High Similarity	NPC123912
0.8791	High Similarity	NPC2983
0.8778	High Similarity	NPC58063
0.8778	High Similarity	NPC475740
0.8776	High Similarity	NPC204833
0.8776	High Similarity	NPC209502
0.8764	High Similarity	NPC470574
0.8764	High Similarity	NPC471224
0.8763	High Similarity	NPC308726
0.8763	High Similarity	NPC119601
0.875	High Similarity	NPC154072
0.875	High Similarity	NPC51370
0.875	High Similarity	NPC287833
0.8737	High Similarity	NPC320306
0.8723	High Similarity	NPC470016
0.8723	High Similarity	NPC317586
0.8723	High Similarity	NPC180950
0.871	High Similarity	NPC474736
0.8696	High Similarity	NPC469400
0.8687	High Similarity	NPC97202
0.8687	High Similarity	NPC214264
0.8687	High Similarity	NPC319077
0.8687	High Similarity	NPC202167
0.8687	High Similarity	NPC296945
0.8687	High Similarity	NPC150531
0.8687	High Similarity	NPC49958
0.8687	High Similarity	NPC302607
0.8687	High Similarity	NPC323834
0.8687	High Similarity	NPC149047
0.8687	High Similarity	NPC260268
0.8687	High Similarity	NPC171137
0.8687	High Similarity	NPC152695
0.8687	High Similarity	NPC48733
0.8687	High Similarity	NPC85829
0.8687	High Similarity	NPC50692
0.8687	High Similarity	NPC476027
0.8681	High Similarity	NPC471724
0.8673	High Similarity	NPC249187
0.8673	High Similarity	NPC247957
0.8673	High Similarity	NPC111323
0.8673	High Similarity	NPC311612
0.8667	High Similarity	NPC31564
0.8667	High Similarity	NPC94755
0.8667	High Similarity	NPC474778
0.8667	High Similarity	NPC145879
0.8667	High Similarity	NPC474732
0.8667	High Similarity	NPC472974
0.8667	High Similarity	NPC474733
0.866	High Similarity	NPC476223
0.866	High Similarity	NPC224720
0.866	High Similarity	NPC476240
0.866	High Similarity	NPC472924
0.8652	High Similarity	NPC85774
0.8652	High Similarity	NPC214043
0.8646	High Similarity	NPC197386
0.8646	High Similarity	NPC471717
0.8636	High Similarity	NPC87489
0.8632	High Similarity	NPC471463
0.8632	High Similarity	NPC305483
0.8632	High Similarity	NPC96859
0.8632	High Similarity	NPC472941
0.8632	High Similarity	NPC160056
0.8632	High Similarity	NPC456
0.8632	High Similarity	NPC328162
0.8632	High Similarity	NPC117133
0.8617	High Similarity	NPC474690
0.8617	High Similarity	NPC472976
0.8617	High Similarity	NPC292793
0.8617	High Similarity	NPC184870
0.8617	High Similarity	NPC472977
0.8617	High Similarity	NPC469406
0.8614	High Similarity	NPC214644
0.8602	High Similarity	NPC472975
0.86	High Similarity	NPC83744
0.86	High Similarity	NPC220229
0.86	High Similarity	NPC185
0.86	High Similarity	NPC472925
0.86	High Similarity	NPC477916
0.86	High Similarity	NPC475060
0.8587	High Similarity	NPC1015
0.8587	High Similarity	NPC186688
0.8587	High Similarity	NPC31985
0.8587	High Similarity	NPC472971
0.8587	High Similarity	NPC214387
0.8587	High Similarity	NPC472970
0.8571	High Similarity	NPC195290
0.8571	High Similarity	NPC136548
0.8571	High Similarity	NPC87351
0.8571	High Similarity	NPC287079
0.8571	High Similarity	NPC187376
0.8571	High Similarity	NPC159046
0.8571	High Similarity	NPC233836
0.8571	High Similarity	NPC141292
0.8571	High Similarity	NPC204450
0.8571	High Similarity	NPC293753
0.8571	High Similarity	NPC234892
0.8557	High Similarity	NPC112167
0.8557	High Similarity	NPC144956
0.8557	High Similarity	NPC327431
0.8557	High Similarity	NPC316964
0.8557	High Similarity	NPC476274
0.8556	High Similarity	NPC469948
0.8542	High Similarity	NPC18509
0.8542	High Similarity	NPC474938
0.8542	High Similarity	NPC474785
0.8539	High Similarity	NPC476082
0.8539	High Similarity	NPC278648
0.8539	High Similarity	NPC64600
0.8526	High Similarity	NPC297199
0.8526	High Similarity	NPC37646
0.8526	High Similarity	NPC200702
0.8526	High Similarity	NPC473170
0.8515	High Similarity	NPC65941
0.8515	High Similarity	NPC295244
0.8515	High Similarity	NPC329417
0.8515	High Similarity	NPC217201
0.8511	High Similarity	NPC109305
0.8511	High Similarity	NPC477520
0.8511	High Similarity	NPC475255
0.8511	High Similarity	NPC134826
0.85	High Similarity	NPC257353
0.8495	Intermediate Similarity	NPC134321
0.8495	Intermediate Similarity	NPC477149
0.8495	Intermediate Similarity	NPC320026
0.8495	Intermediate Similarity	NPC126993
0.8495	Intermediate Similarity	NPC85173
0.8495	Intermediate Similarity	NPC69622
0.8495	Intermediate Similarity	NPC477147
0.8485	Intermediate Similarity	NPC236390
0.8478	Intermediate Similarity	NPC292491
0.8478	Intermediate Similarity	NPC53911
0.8478	Intermediate Similarity	NPC193360
0.8478	Intermediate Similarity	NPC310752
0.8462	Intermediate Similarity	NPC469994
0.8462	Intermediate Similarity	NPC472985
0.8462	Intermediate Similarity	NPC472986
0.8462	Intermediate Similarity	NPC55309
0.8462	Intermediate Similarity	NPC28252
0.8454	Intermediate Similarity	NPC114274
0.8444	Intermediate Similarity	NPC231310
0.8444	Intermediate Similarity	NPC59453
0.8444	Intermediate Similarity	NPC221758
0.8444	Intermediate Similarity	NPC476412
0.8438	Intermediate Similarity	NPC243525
0.8438	Intermediate Similarity	NPC3772
0.8438	Intermediate Similarity	NPC7124
0.8438	Intermediate Similarity	NPC250757
0.8438	Intermediate Similarity	NPC192428
0.8438	Intermediate Similarity	NPC301534
0.8438	Intermediate Similarity	NPC40765
0.8431	Intermediate Similarity	NPC11710
0.8421	Intermediate Similarity	NPC111015
0.8421	Intermediate Similarity	NPC196485
0.8421	Intermediate Similarity	NPC245972
0.8421	Intermediate Similarity	NPC471207

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 NPC259286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1387
0.2-0.3	3928
0.3-0.4	2507
0.4-0.5	703
0.5-0.6	169
0.6-0.7	154
0.7-0.8	125
0.8-0.85	27
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9222	High Similarity	NPD6079	Approved
0.9213	High Similarity	NPD5328	Approved
0.8763	High Similarity	NPD5211	Phase 2
0.8667	High Similarity	NPD3618	Phase 1
0.8632	High Similarity	NPD5222	Approved
0.8632	High Similarity	NPD5221	Approved
0.8632	High Similarity	NPD5220	Clinical (unspecified phase)
0.8586	High Similarity	NPD5141	Approved
0.8557	High Similarity	NPD4696	Approved
0.8557	High Similarity	NPD5286	Approved
0.8557	High Similarity	NPD5285	Approved
0.8542	High Similarity	NPD5173	Approved
0.8542	High Similarity	NPD4755	Approved
0.8511	High Similarity	NPD4202	Approved
0.8469	Intermediate Similarity	NPD5223	Approved
0.8444	Intermediate Similarity	NPD4786	Approved
0.8438	Intermediate Similarity	NPD4697	Phase 3
0.8384	Intermediate Similarity	NPD5226	Approved
0.8384	Intermediate Similarity	NPD4633	Approved
0.8384	Intermediate Similarity	NPD5225	Approved
0.8384	Intermediate Similarity	NPD5224	Approved
0.8367	Intermediate Similarity	NPD4700	Approved
0.83	Intermediate Similarity	NPD5175	Approved
0.83	Intermediate Similarity	NPD5174	Approved
0.8261	Intermediate Similarity	NPD5279	Phase 3
0.8242	Intermediate Similarity	NPD3133	Approved
0.8242	Intermediate Similarity	NPD3665	Phase 1
0.8242	Intermediate Similarity	NPD3666	Approved
0.8222	Intermediate Similarity	NPD3667	Approved
0.8155	Intermediate Similarity	NPD6881	Approved
0.8155	Intermediate Similarity	NPD6899	Approved
0.8137	Intermediate Similarity	NPD7128	Approved
0.8137	Intermediate Similarity	NPD5739	Approved
0.8137	Intermediate Similarity	NPD6675	Approved
0.8137	Intermediate Similarity	NPD6402	Approved
0.8119	Intermediate Similarity	NPD4754	Approved
0.8065	Intermediate Similarity	NPD5690	Phase 2
0.8058	Intermediate Similarity	NPD5697	Approved
0.8022	Intermediate Similarity	NPD4221	Approved
0.8022	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.7981	Intermediate Similarity	NPD4729	Approved
0.7981	Intermediate Similarity	NPD6011	Approved
0.7981	Intermediate Similarity	NPD4730	Approved
0.7981	Intermediate Similarity	NPD7320	Approved
0.7961	Intermediate Similarity	NPD4767	Approved
0.7961	Intermediate Similarity	NPD4768	Approved
0.7957	Intermediate Similarity	NPD5329	Approved
0.7925	Intermediate Similarity	NPD6650	Approved
0.7925	Intermediate Similarity	NPD6649	Approved
0.7925	Intermediate Similarity	NPD6617	Approved
0.7925	Intermediate Similarity	NPD6869	Approved
0.7925	Intermediate Similarity	NPD6847	Approved
0.7925	Intermediate Similarity	NPD8130	Phase 1
0.7905	Intermediate Similarity	NPD6014	Approved
0.7905	Intermediate Similarity	NPD6012	Approved
0.7905	Intermediate Similarity	NPD6373	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.7905	Intermediate Similarity	NPD6013	Approved
0.7885	Intermediate Similarity	NPD5701	Approved
0.7872	Intermediate Similarity	NPD4623	Approved
0.7872	Intermediate Similarity	NPD4519	Discontinued
0.7872	Intermediate Similarity	NPD4694	Approved
0.7872	Intermediate Similarity	NPD5280	Approved
0.785	Intermediate Similarity	NPD6882	Approved
0.785	Intermediate Similarity	NPD8297	Approved
0.7849	Intermediate Similarity	NPD4197	Approved
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.783	Intermediate Similarity	NPD4634	Approved
0.783	Intermediate Similarity	NPD5249	Phase 3
0.783	Intermediate Similarity	NPD5247	Approved
0.783	Intermediate Similarity	NPD5248	Approved
0.783	Intermediate Similarity	NPD5250	Approved
0.783	Intermediate Similarity	NPD5135	Approved
0.783	Intermediate Similarity	NPD5169	Approved
0.783	Intermediate Similarity	NPD5251	Approved
0.783	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5128	Approved
0.781	Intermediate Similarity	NPD5168	Approved
0.7778	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD4629	Approved
0.7757	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD5217	Approved
0.7757	Intermediate Similarity	NPD5215	Approved
0.7757	Intermediate Similarity	NPD5216	Approved
0.7757	Intermediate Similarity	NPD5127	Approved
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7684	Intermediate Similarity	NPD5205	Approved
0.7684	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4688	Approved
0.7684	Intermediate Similarity	NPD4689	Approved
0.7684	Intermediate Similarity	NPD4690	Approved
0.7684	Intermediate Similarity	NPD4693	Phase 3
0.7684	Intermediate Similarity	NPD4138	Approved
0.7653	Intermediate Similarity	NPD5281	Approved
0.7653	Intermediate Similarity	NPD5284	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7624	Intermediate Similarity	NPD6084	Phase 2
0.7624	Intermediate Similarity	NPD6083	Phase 2
0.7615	Intermediate Similarity	NPD4632	Approved
0.7609	Intermediate Similarity	NPD7525	Registered
0.76	Intermediate Similarity	NPD5695	Phase 3
0.7579	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6399	Phase 3
0.7553	Intermediate Similarity	NPD4788	Approved
0.7549	Intermediate Similarity	NPD7638	Approved
0.7545	Intermediate Similarity	NPD5167	Approved
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7477	Intermediate Similarity	NPD6868	Approved
0.7474	Intermediate Similarity	NPD3668	Phase 3
0.7444	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD6942	Approved
0.7434	Intermediate Similarity	NPD7100	Approved
0.7434	Intermediate Similarity	NPD7101	Approved
0.7423	Intermediate Similarity	NPD3573	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7411	Intermediate Similarity	NPD6317	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7391	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4096	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5737	Approved
0.7347	Intermediate Similarity	NPD4518	Approved
0.7347	Intermediate Similarity	NPD6903	Approved
0.7345	Intermediate Similarity	NPD6314	Approved
0.7345	Intermediate Similarity	NPD6313	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.7333	Intermediate Similarity	NPD5733	Approved
0.7333	Intermediate Similarity	NPD4687	Approved
0.7321	Intermediate Similarity	NPD6274	Approved
0.729	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD7902	Approved
0.7255	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6370	Approved
0.7228	Intermediate Similarity	NPD5133	Approved
0.7217	Intermediate Similarity	NPD6059	Approved
0.7217	Intermediate Similarity	NPD6319	Approved
0.7216	Intermediate Similarity	NPD1696	Phase 3
0.7212	Intermediate Similarity	NPD5696	Approved
0.72	Intermediate Similarity	NPD5207	Approved
0.7191	Intermediate Similarity	NPD4747	Approved
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7174	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5983	Phase 2
0.7155	Intermediate Similarity	NPD6909	Approved
0.7155	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6016	Approved
0.7155	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD6404	Discontinued
0.7129	Intermediate Similarity	NPD6050	Approved
0.7129	Intermediate Similarity	NPD6411	Approved
0.7129	Intermediate Similarity	NPD5694	Approved
0.7119	Intermediate Similarity	NPD7492	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5276	Approved
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6904	Approved
0.71	Intermediate Similarity	NPD6080	Approved
0.71	Intermediate Similarity	NPD6673	Approved
0.7094	Intermediate Similarity	NPD5988	Approved
0.7079	Intermediate Similarity	NPD4137	Phase 3
0.7065	Intermediate Similarity	NPD8264	Approved
0.7065	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD5778	Approved
0.7059	Intermediate Similarity	NPD6336	Discontinued
0.7053	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7053	Intermediate Similarity	NPD4748	Discontinued
0.7048	Intermediate Similarity	NPD5290	Discontinued
0.7041	Intermediate Similarity	NPD1694	Approved
0.703	Intermediate Similarity	NPD5692	Phase 3
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD4691	Approved
0.7	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD5208	Approved
0.699	Remote Similarity	NPD6001	Approved
0.699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7900	Approved
0.697	Remote Similarity	NPD6098	Approved
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD5693	Phase 1

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