NPASS Compound

Structure

NPC138757 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 2.3269 -8.8880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2221 1.7359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5138 2.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3630 0.5699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2540 -0.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5546 -8.2954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6816 -7.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9093 -6.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0364 -5.7725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2641 -5.1799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3911 -4.2147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3812 -3.6221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2541 -2.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9991 1.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2404 -1.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1839 1.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1412 -2.1398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5337 1.0475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0317 1.3381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5138 -1.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 -0.7266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6874 0.7587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0265 -2.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5784 -0.2087 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6474 0.3299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8353 -0.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4707 0.1806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5138 0.5138 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 0.7339 -2.9121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9258 -2.4368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5148 -0.1121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5414 -1.7818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7323 -0.6415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8994 -1.0991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 25 1 0 0 0 0 19 29 1 6 0 0 0 20 27 1 0 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 14 1 1 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 32 2 0 0 0 0 23 36 1 0 0 0 0 24 28 1 1 0 0 0 25 30 1 1 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 26 34 2 0 0 0 0 27 30 1 1 0 0 0 27 36 1 0 0 0 0 29 30 1 1 0 0 0 30 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	741.41
Volume:	780.367
LogP:	3.955
LogD:	3.386
LogS:	-4.601
# Rotatable Bonds:	8
TPSA:	145.43
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	5.19
Fsp3:	0.524
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.014
MDCK Permeability:	8.196610724553466e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.334
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	95.5416488647461%
Volume Distribution (VD):	0.443
Pgp-substrate:	1.1239640712738037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.29
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.478
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	4.681
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.8
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.751
Skin Sensitization:	0.051
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC138757

Natural Product ID:	NPC138757
*Common Name:**	BMSQOSCSLGJQPZ-FUXMVPHISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BMSQOSCSLGJQPZ-FUXMVPHISA-N
Standard InCHI:	InChI=1S/C30H42O6/c1-6-7-8-9-10-11-12-13-23(32)36-27-20(17-31)15-21-24-22(28(24,4)5)14-19(3)29(26(21)34)16-18(2)25(33)30(27,29)35/h10-13,15-16,19,21-22,24-25,27,31,33,35H,6-9,14,17H2,1-5H3/b11-10+,13-12+/t19-,21+,22-,24+,25+,27-,29+,30-/m1/s1
SMILES:	CCCCC/C=C/C=C/C(=O)O[C@@H]1C(=C[C@@H]2C(=O)[C@@]3([C@@]1(O)[C@@H](O)C(=C3)C)[C@H](C)C[C@@H]1[C@H]2C1(C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486879
PubChem CID:	12040017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	>	75.0	%	PMID[481463]

☑ 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 NPC138757 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	245
0.1-0.2	1340
0.2-0.3	4509
0.3-0.4	8379
0.4-0.5	15456
0.5-0.6	8138
0.6-0.7	3729
0.7-0.8	828
0.8-0.85	38
0.85-0.9	5
0.9-0.95	16
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC46269
0.9904	High Similarity	NPC106395
0.981	High Similarity	NPC133677
0.981	High Similarity	NPC67290
0.981	High Similarity	NPC138303
0.9808	High Similarity	NPC123855
0.9808	High Similarity	NPC76550
0.9709	High Similarity	NPC47951
0.9615	High Similarity	NPC257240
0.9333	High Similarity	NPC477102
0.9245	High Similarity	NPC477103
0.9238	High Similarity	NPC308191
0.9231	High Similarity	NPC179891
0.8981	High Similarity	NPC287311
0.8692	High Similarity	NPC473488
0.8692	High Similarity	NPC475661
0.8611	High Similarity	NPC473911
0.8544	High Similarity	NPC261341
0.8426	Intermediate Similarity	NPC203659
0.8362	Intermediate Similarity	NPC475885
0.8333	Intermediate Similarity	NPC110989
0.8276	Intermediate Similarity	NPC236918
0.8276	Intermediate Similarity	NPC156745
0.8257	Intermediate Similarity	NPC309190
0.8257	Intermediate Similarity	NPC100487
0.8241	Intermediate Similarity	NPC225353
0.8205	Intermediate Similarity	NPC329080
0.8205	Intermediate Similarity	NPC472759
0.8182	Intermediate Similarity	NPC236999
0.8182	Intermediate Similarity	NPC243998
0.8165	Intermediate Similarity	NPC475945
0.8165	Intermediate Similarity	NPC475871
0.8136	Intermediate Similarity	NPC470829
0.8136	Intermediate Similarity	NPC473228
0.8131	Intermediate Similarity	NPC141191
0.812	Intermediate Similarity	NPC477092
0.8108	Intermediate Similarity	NPC26617
0.8103	Intermediate Similarity	NPC471145
0.8095	Intermediate Similarity	NPC167219
0.8091	Intermediate Similarity	NPC474741
0.8083	Intermediate Similarity	NPC145238
0.8073	Intermediate Similarity	NPC474747
0.8073	Intermediate Similarity	NPC86077
0.8051	Intermediate Similarity	NPC19336
0.8051	Intermediate Similarity	NPC185876
0.8037	Intermediate Similarity	NPC169205
0.8037	Intermediate Similarity	NPC477949
0.8034	Intermediate Similarity	NPC475401
0.8034	Intermediate Similarity	NPC146280
0.8034	Intermediate Similarity	NPC472760
0.8034	Intermediate Similarity	NPC124676
0.8019	Intermediate Similarity	NPC304886
0.8018	Intermediate Similarity	NPC223450
0.8017	Intermediate Similarity	NPC154363
0.8017	Intermediate Similarity	NPC471127
0.8017	Intermediate Similarity	NPC234858
0.8	Intermediate Similarity	NPC472399
0.8	Intermediate Similarity	NPC472755
0.7982	Intermediate Similarity	NPC474742
0.7982	Intermediate Similarity	NPC472753
0.7982	Intermediate Similarity	NPC71680
0.7982	Intermediate Similarity	NPC150923
0.7981	Intermediate Similarity	NPC473448
0.7966	Intermediate Similarity	NPC180640
0.7951	Intermediate Similarity	NPC471940
0.7949	Intermediate Similarity	NPC10721
0.7949	Intermediate Similarity	NPC475305
0.7944	Intermediate Similarity	NPC185553
0.7931	Intermediate Similarity	NPC472400
0.7928	Intermediate Similarity	NPC472756
0.7925	Intermediate Similarity	NPC65829
0.7917	Intermediate Similarity	NPC257017
0.7917	Intermediate Similarity	NPC162009
0.7909	Intermediate Similarity	NPC472754
0.7905	Intermediate Similarity	NPC476705
0.7899	Intermediate Similarity	NPC145182
0.7899	Intermediate Similarity	NPC157252
0.7899	Intermediate Similarity	NPC471128
0.7899	Intermediate Similarity	NPC471126
0.7895	Intermediate Similarity	NPC15551
0.7881	Intermediate Similarity	NPC13710
0.7869	Intermediate Similarity	NPC471939
0.785	Intermediate Similarity	NPC469873
0.785	Intermediate Similarity	NPC193645
0.785	Intermediate Similarity	NPC275960
0.785	Intermediate Similarity	NPC90121
0.785	Intermediate Similarity	NPC48803
0.7845	Intermediate Similarity	NPC71889
0.7845	Intermediate Similarity	NPC472757
0.7833	Intermediate Similarity	NPC472401
0.7833	Intermediate Similarity	NPC52839
0.7826	Intermediate Similarity	NPC470961
0.7818	Intermediate Similarity	NPC477950
0.7818	Intermediate Similarity	NPC206079
0.7818	Intermediate Similarity	NPC171759
0.7818	Intermediate Similarity	NPC116139
0.7798	Intermediate Similarity	NPC64742
0.7798	Intermediate Similarity	NPC244411
0.7798	Intermediate Similarity	NPC161855
0.7797	Intermediate Similarity	NPC475323
0.7797	Intermediate Similarity	NPC156252
0.7797	Intermediate Similarity	NPC471146
0.7797	Intermediate Similarity	NPC153651
0.7787	Intermediate Similarity	NPC473919
0.7787	Intermediate Similarity	NPC473709
0.7787	Intermediate Similarity	NPC8374
0.7778	Intermediate Similarity	NPC305044
0.7778	Intermediate Similarity	NPC265290
0.7778	Intermediate Similarity	NPC474872
0.7778	Intermediate Similarity	NPC473291
0.7769	Intermediate Similarity	NPC19464
0.7768	Intermediate Similarity	NPC220964
0.7768	Intermediate Similarity	NPC475676
0.7759	Intermediate Similarity	NPC241477
0.7759	Intermediate Similarity	NPC191620
0.7757	Intermediate Similarity	NPC323008
0.7757	Intermediate Similarity	NPC470010
0.7757	Intermediate Similarity	NPC477131
0.7757	Intermediate Similarity	NPC470013
0.7757	Intermediate Similarity	NPC198853
0.7757	Intermediate Similarity	NPC262133
0.775	Intermediate Similarity	NPC474370
0.7748	Intermediate Similarity	NPC118405
0.7748	Intermediate Similarity	NPC66110
0.7739	Intermediate Similarity	NPC29133
0.7739	Intermediate Similarity	NPC181298
0.7731	Intermediate Similarity	NPC472397
0.7731	Intermediate Similarity	NPC288679
0.7731	Intermediate Similarity	NPC471125
0.7731	Intermediate Similarity	NPC171905
0.7731	Intermediate Similarity	NPC186525
0.7731	Intermediate Similarity	NPC472758
0.7727	Intermediate Similarity	NPC288876
0.7727	Intermediate Similarity	NPC469864
0.7727	Intermediate Similarity	NPC469872
0.7727	Intermediate Similarity	NPC475053
0.7719	Intermediate Similarity	NPC233379
0.7719	Intermediate Similarity	NPC14862
0.7719	Intermediate Similarity	NPC474664
0.7706	Intermediate Similarity	NPC161493
0.7706	Intermediate Similarity	NPC108475
0.7706	Intermediate Similarity	NPC170143
0.7706	Intermediate Similarity	NPC40812
0.7706	Intermediate Similarity	NPC213947
0.7706	Intermediate Similarity	NPC311904
0.7705	Intermediate Similarity	NPC473802
0.7699	Intermediate Similarity	NPC54737
0.7692	Intermediate Similarity	NPC469496
0.7692	Intermediate Similarity	NPC469454
0.7692	Intermediate Similarity	NPC209058
0.7692	Intermediate Similarity	NPC469463
0.7686	Intermediate Similarity	NPC46570
0.7686	Intermediate Similarity	NPC67569
0.7685	Intermediate Similarity	NPC67584
0.7685	Intermediate Similarity	NPC36954
0.7685	Intermediate Similarity	NPC270013
0.7685	Intermediate Similarity	NPC52044
0.7685	Intermediate Similarity	NPC14961
0.7685	Intermediate Similarity	NPC220221
0.7679	Intermediate Similarity	NPC124881
0.7679	Intermediate Similarity	NPC475873
0.7679	Intermediate Similarity	NPC4620
0.7679	Intermediate Similarity	NPC183570
0.7672	Intermediate Similarity	NPC474871
0.7672	Intermediate Similarity	NPC317107
0.7672	Intermediate Similarity	NPC475495
0.7672	Intermediate Similarity	NPC475937
0.7672	Intermediate Similarity	NPC260786
0.7672	Intermediate Similarity	NPC96739
0.7672	Intermediate Similarity	NPC158523
0.7672	Intermediate Similarity	NPC174471
0.767	Intermediate Similarity	NPC11804
0.7667	Intermediate Similarity	NPC255081
0.7667	Intermediate Similarity	NPC264954
0.7667	Intermediate Similarity	NPC275696
0.7667	Intermediate Similarity	NPC5991
0.7667	Intermediate Similarity	NPC22628
0.7667	Intermediate Similarity	NPC5989
0.7667	Intermediate Similarity	NPC471108
0.7664	Intermediate Similarity	NPC475912
0.7664	Intermediate Similarity	NPC469645
0.7664	Intermediate Similarity	NPC469692
0.7658	Intermediate Similarity	NPC164598
0.7658	Intermediate Similarity	NPC62670
0.7658	Intermediate Similarity	NPC474339
0.7652	Intermediate Similarity	NPC475274
0.7652	Intermediate Similarity	NPC273433
0.7652	Intermediate Similarity	NPC15218
0.7647	Intermediate Similarity	NPC312824
0.7647	Intermediate Similarity	NPC470493
0.7647	Intermediate Similarity	NPC183580
0.7642	Intermediate Similarity	NPC145666
0.7642	Intermediate Similarity	NPC144625
0.7642	Intermediate Similarity	NPC469368
0.7636	Intermediate Similarity	NPC221615
0.7636	Intermediate Similarity	NPC83895
0.7636	Intermediate Similarity	NPC187761
0.7634	Intermediate Similarity	NPC52523
0.7634	Intermediate Similarity	NPC217673
0.7632	Intermediate Similarity	NPC72813

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 NPC138757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1802
0.2-0.3	3595
0.3-0.4	2316
0.4-0.5	859
0.5-0.6	302
0.6-0.7	42
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9615	High Similarity	NPD6371	Approved
0.8108	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD7838	Discovery
0.7407	Intermediate Similarity	NPD7983	Approved
0.7379	Intermediate Similarity	NPD5209	Approved
0.7333	Intermediate Similarity	NPD5363	Approved
0.7315	Intermediate Similarity	NPD46	Approved
0.7315	Intermediate Similarity	NPD6698	Approved
0.7222	Intermediate Similarity	NPD1695	Approved
0.7168	Intermediate Similarity	NPD4225	Approved
0.7048	Intermediate Similarity	NPD4269	Approved
0.7048	Intermediate Similarity	NPD4270	Approved
0.7027	Intermediate Similarity	NPD5778	Approved
0.7027	Intermediate Similarity	NPD5779	Approved
0.7018	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5362	Discontinued
0.6975	Remote Similarity	NPD6686	Approved
0.6964	Remote Similarity	NPD5282	Discontinued
0.6952	Remote Similarity	NPD5369	Approved
0.6944	Remote Similarity	NPD5786	Approved
0.6937	Remote Similarity	NPD7637	Suspended
0.6897	Remote Similarity	NPD5344	Discontinued
0.6857	Remote Similarity	NPD4252	Approved
0.6822	Remote Similarity	NPD7154	Phase 3
0.681	Remote Similarity	NPD6648	Approved
0.6772	Remote Similarity	NPD6319	Approved
0.6748	Remote Similarity	NPD6053	Discontinued
0.6719	Remote Similarity	NPD8517	Approved
0.6719	Remote Similarity	NPD8513	Phase 3
0.6719	Remote Similarity	NPD8515	Approved
0.6719	Remote Similarity	NPD8516	Approved
0.6698	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4821	Approved
0.6698	Remote Similarity	NPD4822	Approved
0.6698	Remote Similarity	NPD4819	Approved
0.6698	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8273	Phase 1
0.6637	Remote Similarity	NPD6411	Approved
0.6617	Remote Similarity	NPD7319	Approved
0.6613	Remote Similarity	NPD8297	Approved
0.6589	Remote Similarity	NPD7503	Approved
0.6577	Remote Similarity	NPD4250	Approved
0.6577	Remote Similarity	NPD4251	Approved
0.6574	Remote Similarity	NPD6435	Approved
0.6565	Remote Similarity	NPD7492	Approved
0.656	Remote Similarity	NPD4632	Approved
0.6557	Remote Similarity	NPD6899	Approved
0.6557	Remote Similarity	NPD6881	Approved
0.6552	Remote Similarity	NPD7839	Suspended
0.6545	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6650	Approved
0.6532	Remote Similarity	NPD6649	Approved
0.6525	Remote Similarity	NPD7640	Approved
0.6525	Remote Similarity	NPD7639	Approved
0.6515	Remote Similarity	NPD7507	Approved
0.6515	Remote Similarity	NPD6616	Approved
0.6512	Remote Similarity	NPD6054	Approved
0.6509	Remote Similarity	NPD4268	Approved
0.6509	Remote Similarity	NPD4271	Approved
0.6504	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6084	Phase 2
0.6496	Remote Similarity	NPD6083	Phase 2
0.6491	Remote Similarity	NPD5284	Approved
0.6491	Remote Similarity	NPD5281	Approved
0.6489	Remote Similarity	NPD7604	Phase 2
0.6486	Remote Similarity	NPD4249	Approved
0.6475	Remote Similarity	NPD5697	Approved
0.6475	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD8074	Phase 3
0.6466	Remote Similarity	NPD7078	Approved
0.646	Remote Similarity	NPD6101	Approved
0.646	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7290	Approved
0.6452	Remote Similarity	NPD6883	Approved
0.6452	Remote Similarity	NPD4634	Approved
0.6452	Remote Similarity	NPD7102	Approved
0.6441	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD7524	Approved
0.6423	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7736	Approved
0.6412	Remote Similarity	NPD6370	Approved
0.64	Remote Similarity	NPD6847	Approved
0.64	Remote Similarity	NPD8130	Phase 1
0.64	Remote Similarity	NPD6869	Approved
0.64	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD6402	Approved
0.6393	Remote Similarity	NPD5739	Approved
0.6393	Remote Similarity	NPD6675	Approved
0.6393	Remote Similarity	NPD7128	Approved
0.6389	Remote Similarity	NPD5368	Approved
0.6371	Remote Similarity	NPD6014	Approved
0.6371	Remote Similarity	NPD6012	Approved
0.6371	Remote Similarity	NPD6373	Approved
0.6371	Remote Similarity	NPD6013	Approved
0.6371	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD5331	Approved
0.6364	Remote Similarity	NPD7642	Approved
0.6364	Remote Similarity	NPD7830	Approved
0.6364	Remote Similarity	NPD7829	Approved
0.6364	Remote Similarity	NPD5332	Approved
0.6349	Remote Similarity	NPD6882	Approved
0.6336	Remote Similarity	NPD6016	Approved
0.6336	Remote Similarity	NPD6015	Approved
0.633	Remote Similarity	NPD4790	Discontinued
0.6325	Remote Similarity	NPD5695	Phase 3
0.632	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5696	Approved
0.6293	Remote Similarity	NPD6399	Phase 3
0.629	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD7320	Approved
0.6288	Remote Similarity	NPD5988	Approved
0.6286	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5211	Phase 2
0.6279	Remote Similarity	NPD6009	Approved
0.6277	Remote Similarity	NPD7260	Phase 2
0.6273	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6059	Approved
0.626	Remote Similarity	NPD6008	Approved
0.6231	Remote Similarity	NPD7328	Approved
0.6231	Remote Similarity	NPD7327	Approved
0.6222	Remote Similarity	NPD8293	Discontinued
0.6216	Remote Similarity	NPD6695	Phase 3
0.6212	Remote Similarity	NPD8033	Approved
0.6212	Remote Similarity	NPD5983	Phase 2
0.621	Remote Similarity	NPD5701	Approved
0.6186	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5210	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7516	Approved
0.6179	Remote Similarity	NPD5141	Approved
0.6174	Remote Similarity	NPD5370	Suspended
0.6154	Remote Similarity	NPD7500	Approved
0.6148	Remote Similarity	NPD8451	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6136	Remote Similarity	NPD8377	Approved
0.6136	Remote Similarity	NPD8294	Approved
0.6126	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5207	Approved
0.6116	Remote Similarity	NPD4696	Approved
0.6116	Remote Similarity	NPD5286	Approved
0.6116	Remote Similarity	NPD5285	Approved
0.6107	Remote Similarity	NPD7641	Discontinued
0.6106	Remote Similarity	NPD1696	Phase 3
0.6103	Remote Similarity	NPD8448	Approved
0.6091	Remote Similarity	NPD7332	Phase 2
0.609	Remote Similarity	NPD8296	Approved
0.609	Remote Similarity	NPD8379	Approved
0.609	Remote Similarity	NPD8335	Approved
0.609	Remote Similarity	NPD8378	Approved
0.609	Remote Similarity	NPD8444	Approved
0.609	Remote Similarity	NPD8380	Approved
0.608	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8039	Approved
0.6074	Remote Similarity	NPD8340	Approved
0.6074	Remote Similarity	NPD8299	Approved
0.6074	Remote Similarity	NPD8341	Approved
0.6074	Remote Similarity	NPD8342	Approved
0.6068	Remote Similarity	NPD6050	Approved
0.6068	Remote Similarity	NPD5694	Approved
0.6068	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5693	Phase 1
0.6061	Remote Similarity	NPD7100	Approved
0.6061	Remote Similarity	NPD7101	Approved
0.6061	Remote Similarity	NPD4522	Approved
0.6053	Remote Similarity	NPD7146	Approved
0.6053	Remote Similarity	NPD7334	Approved
0.6053	Remote Similarity	NPD6409	Approved
0.6053	Remote Similarity	NPD6684	Approved
0.6053	Remote Similarity	NPD5330	Approved
0.6053	Remote Similarity	NPD7521	Approved
0.6047	Remote Similarity	NPD8133	Approved
0.6036	Remote Similarity	NPD6902	Approved
0.6034	Remote Similarity	NPD4753	Phase 2
0.6018	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5225	Approved
0.6016	Remote Similarity	NPD4633	Approved
0.6016	Remote Similarity	NPD5226	Approved
0.6016	Remote Similarity	NPD5224	Approved
0.6016	Remote Similarity	NPD7632	Discontinued
0.6016	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD8328	Phase 3
0.5985	Remote Similarity	NPD6335	Approved
0.5983	Remote Similarity	NPD5692	Phase 3
0.5971	Remote Similarity	NPD8391	Approved
0.5971	Remote Similarity	NPD8392	Approved
0.5971	Remote Similarity	NPD8390	Approved
0.5971	Remote Similarity	NPD5956	Approved
0.5968	Remote Similarity	NPD5174	Approved
0.5968	Remote Similarity	NPD5175	Approved
0.5968	Remote Similarity	NPD6647	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data