NPASS Compound

Structure

NPC119550 OpenBabel07101718232D 37 39 0 0 1 0 0 0 0 0999 V2000 3.9937 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3765 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3546 1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -0.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0238 2.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 7 34 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 6 0 0 0 19 30 2 0 0 0 0 19 35 1 0 0 0 0 20 36 1 6 0 0 0 21 26 1 0 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 31 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 25 29 1 6 0 0 0 25 33 1 0 0 0 0 26 34 1 6 0 0 0 26 37 1 0 0 0 0 27 29 1 6 0 0 0 27 35 1 0 0 0 0 27 37 1 0 0 0 0 28 6 1 1 0 0 0 29 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.3
Volume:	541.61
LogP:	4.298
LogD:	3.376
LogS:	-4.54
# Rotatable Bonds:	12
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	5.818
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
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:	-4.716
MDCK Permeability:	7.653542706975713e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.074

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	93.27899932861328%
Volume Distribution (VD):	1.697
Pgp-substrate:	3.4465889930725098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	3.965
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.685
Drug-inuced Liver Injury (DILI):	0.722
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.559
Skin Sensitization:	0.41
Carcinogencity:	0.683
Eye Corrosion:	0.006
Eye Irritation:	0.013
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC119550

Natural Product ID:	NPC119550
*Common Name:**	Caseargrewins K
IUPAC Name:	[(1S,3S,5R,6aS,7S,8S,9R,10R,10aS)-1-acetyloxy-9,10-dihydroxy-3-methoxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] hexanoate
Synonyms:	caseargrewins K
Standard InCHIKey:	DFOVJJUJVJRZRW-GYNHMMAVSA-N
Standard InCHI:	InChI=1S/C29H44O8/c1-8-10-11-12-23(31)36-20-15-21-26(34-7)37-27(35-19(5)30)29(21)22(16-20)28(6,14-13-17(3)9-2)18(4)24(32)25(29)33/h9,13,15,18,20,22,24-27,32-33H,2,8,10-12,14,16H2,1,3-7H3/b17-13-/t18-,20+,22+,24-,25+,26+,27-,28-,29-/m1/s1
SMILES:	CCCCCC(=O)O[C@H]1C=C2[C@@H](OC)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(/C)C=C)[C@H](C)[C@H]([C@@H]3O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL437186
PubChem CID:	16756992
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	5.11	ug.mL-1	PMID[455080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.4	ug.mL-1	PMID[455080]

☑ 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 NPC119550 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	198
0.1-0.2	1036
0.2-0.3	3569
0.3-0.4	6460
0.4-0.5	13210
0.5-0.6	8584
0.6-0.7	6441
0.7-0.8	2990
0.8-0.85	113
0.85-0.9	29
0.9-0.95	47
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC311223
0.9706	High Similarity	NPC316974
0.9703	High Similarity	NPC125423
0.9703	High Similarity	NPC88013
0.9703	High Similarity	NPC184512
0.9608	High Similarity	NPC217921
0.9608	High Similarity	NPC48548
0.9608	High Similarity	NPC135015
0.9608	High Similarity	NPC128795
0.9604	High Similarity	NPC252296
0.9515	High Similarity	NPC40728
0.9505	High Similarity	NPC473207
0.9505	High Similarity	NPC470321
0.9505	High Similarity	NPC81567
0.9505	High Similarity	NPC201880
0.9505	High Similarity	NPC264867
0.9406	High Similarity	NPC127933
0.9406	High Similarity	NPC7644
0.9406	High Similarity	NPC134270
0.9406	High Similarity	NPC475889
0.9406	High Similarity	NPC7613
0.9307	High Similarity	NPC471363
0.9307	High Similarity	NPC238397
0.9238	High Similarity	NPC316708
0.9151	High Similarity	NPC470026
0.9109	High Similarity	NPC473204
0.9065	High Similarity	NPC317460
0.9065	High Similarity	NPC328074
0.9065	High Similarity	NPC321272
0.9065	High Similarity	NPC470025
0.901	High Similarity	NPC476800
0.901	High Similarity	NPC471366
0.901	High Similarity	NPC472186
0.901	High Similarity	NPC318917
0.8981	High Similarity	NPC470027
0.8972	High Similarity	NPC17791
0.8952	High Similarity	NPC109376
0.8922	High Similarity	NPC472187
0.8922	High Similarity	NPC473545
0.8911	High Similarity	NPC472188
0.8868	High Similarity	NPC224660
0.8868	High Similarity	NPC470024
0.8857	High Similarity	NPC172867
0.8857	High Similarity	NPC218158
0.8812	High Similarity	NPC311166
0.8812	High Similarity	NPC171598
0.8774	High Similarity	NPC293512
0.875	High Similarity	NPC122971
0.8725	High Similarity	NPC98112
0.8713	High Similarity	NPC471362
0.8713	High Similarity	NPC471372
0.8713	High Similarity	NPC472189
0.8661	High Similarity	NPC473617
0.8661	High Similarity	NPC473828
0.8636	High Similarity	NPC293658
0.8636	High Similarity	NPC474410
0.8614	High Similarity	NPC88507
0.8609	High Similarity	NPC41129
0.8532	High Similarity	NPC83005
0.8505	High Similarity	NPC82251
0.8468	Intermediate Similarity	NPC311592
0.8468	Intermediate Similarity	NPC75167
0.8421	Intermediate Similarity	NPC477071
0.8411	Intermediate Similarity	NPC222161
0.8407	Intermediate Similarity	NPC23046
0.8407	Intermediate Similarity	NPC473968
0.8407	Intermediate Similarity	NPC473405
0.8393	Intermediate Similarity	NPC475163
0.8393	Intermediate Similarity	NPC181145
0.8381	Intermediate Similarity	NPC228251
0.8381	Intermediate Similarity	NPC219285
0.8381	Intermediate Similarity	NPC477968
0.8381	Intermediate Similarity	NPC477972
0.8381	Intermediate Similarity	NPC477971
0.8381	Intermediate Similarity	NPC20113
0.8381	Intermediate Similarity	NPC161527
0.8378	Intermediate Similarity	NPC125923
0.8378	Intermediate Similarity	NPC65590
0.8378	Intermediate Similarity	NPC212968
0.8378	Intermediate Similarity	NPC64106
0.8364	Intermediate Similarity	NPC177047
0.8333	Intermediate Similarity	NPC239961
0.8333	Intermediate Similarity	NPC471548
0.8319	Intermediate Similarity	NPC471816
0.8318	Intermediate Similarity	NPC23584
0.8318	Intermediate Similarity	NPC471364
0.8318	Intermediate Similarity	NPC132395
0.8318	Intermediate Similarity	NPC471365
0.8304	Intermediate Similarity	NPC157441
0.8304	Intermediate Similarity	NPC264153
0.8302	Intermediate Similarity	NPC198992
0.8302	Intermediate Similarity	NPC280991
0.8288	Intermediate Similarity	NPC263827
0.8288	Intermediate Similarity	NPC250481
0.8288	Intermediate Similarity	NPC292196
0.8288	Intermediate Similarity	NPC190837
0.8288	Intermediate Similarity	NPC285410
0.8276	Intermediate Similarity	NPC170084
0.8276	Intermediate Similarity	NPC476204
0.8273	Intermediate Similarity	NPC143706
0.8273	Intermediate Similarity	NPC472534
0.8273	Intermediate Similarity	NPC206618
0.8261	Intermediate Similarity	NPC475775
0.8261	Intermediate Similarity	NPC470914
0.8261	Intermediate Similarity	NPC476529
0.8257	Intermediate Similarity	NPC472390
0.8246	Intermediate Similarity	NPC474483
0.8241	Intermediate Similarity	NPC470768
0.8235	Intermediate Similarity	NPC470780
0.823	Intermediate Similarity	NPC469877
0.823	Intermediate Similarity	NPC470919
0.823	Intermediate Similarity	NPC472274
0.823	Intermediate Similarity	NPC220293
0.8224	Intermediate Similarity	NPC472552
0.8224	Intermediate Similarity	NPC273005
0.8224	Intermediate Similarity	NPC11956
0.8224	Intermediate Similarity	NPC31058
0.8224	Intermediate Similarity	NPC470571
0.8224	Intermediate Similarity	NPC469606
0.8218	Intermediate Similarity	NPC470819
0.8214	Intermediate Similarity	NPC194951
0.8214	Intermediate Similarity	NPC161434
0.8214	Intermediate Similarity	NPC116794
0.8214	Intermediate Similarity	NPC12046
0.8214	Intermediate Similarity	NPC302146
0.8214	Intermediate Similarity	NPC195132
0.8214	Intermediate Similarity	NPC174836
0.8214	Intermediate Similarity	NPC473125
0.8198	Intermediate Similarity	NPC274507
0.8198	Intermediate Similarity	NPC110139
0.8198	Intermediate Similarity	NPC220984
0.8198	Intermediate Similarity	NPC46407
0.8198	Intermediate Similarity	NPC75747
0.8198	Intermediate Similarity	NPC127153
0.8198	Intermediate Similarity	NPC7870
0.8198	Intermediate Similarity	NPC68419
0.8198	Intermediate Similarity	NPC199457
0.8198	Intermediate Similarity	NPC102914
0.8198	Intermediate Similarity	NPC108709
0.8198	Intermediate Similarity	NPC235014
0.8198	Intermediate Similarity	NPC129340
0.8198	Intermediate Similarity	NPC101450
0.819	Intermediate Similarity	NPC239547
0.819	Intermediate Similarity	NPC91197
0.819	Intermediate Similarity	NPC125551
0.819	Intermediate Similarity	NPC107338
0.819	Intermediate Similarity	NPC48692
0.819	Intermediate Similarity	NPC155319
0.819	Intermediate Similarity	NPC96597
0.819	Intermediate Similarity	NPC109607
0.819	Intermediate Similarity	NPC309503
0.8182	Intermediate Similarity	NPC38948
0.8182	Intermediate Similarity	NPC219900
0.8182	Intermediate Similarity	NPC177524
0.8182	Intermediate Similarity	NPC392
0.8174	Intermediate Similarity	NPC45475
0.8174	Intermediate Similarity	NPC284707
0.8173	Intermediate Similarity	NPC286612
0.8173	Intermediate Similarity	NPC230347
0.8173	Intermediate Similarity	NPC275310
0.8165	Intermediate Similarity	NPC470767
0.8165	Intermediate Similarity	NPC470763
0.8165	Intermediate Similarity	NPC127609
0.8165	Intermediate Similarity	NPC469607
0.8158	Intermediate Similarity	NPC474046
0.8158	Intermediate Similarity	NPC259306
0.8158	Intermediate Similarity	NPC470628
0.8148	Intermediate Similarity	NPC474124
0.8148	Intermediate Similarity	NPC281378
0.8148	Intermediate Similarity	NPC120009
0.8142	Intermediate Similarity	NPC269315
0.8142	Intermediate Similarity	NPC469496
0.8142	Intermediate Similarity	NPC251309
0.8142	Intermediate Similarity	NPC290608
0.8142	Intermediate Similarity	NPC271138
0.8142	Intermediate Similarity	NPC40133
0.8142	Intermediate Similarity	NPC44298
0.8142	Intermediate Similarity	NPC473128
0.8142	Intermediate Similarity	NPC469463
0.8142	Intermediate Similarity	NPC49413
0.8142	Intermediate Similarity	NPC469454
0.8137	Intermediate Similarity	NPC471371
0.8137	Intermediate Similarity	NPC469403
0.8137	Intermediate Similarity	NPC470817
0.8137	Intermediate Similarity	NPC471370
0.8131	Intermediate Similarity	NPC475617
0.8131	Intermediate Similarity	NPC154127
0.8131	Intermediate Similarity	NPC472554
0.8125	Intermediate Similarity	NPC179434
0.8125	Intermediate Similarity	NPC108748
0.8125	Intermediate Similarity	NPC297208
0.8125	Intermediate Similarity	NPC30397
0.8125	Intermediate Similarity	NPC235841
0.8125	Intermediate Similarity	NPC211798
0.8125	Intermediate Similarity	NPC191763
0.8125	Intermediate Similarity	NPC473481
0.8113	Intermediate Similarity	NPC477928
0.8113	Intermediate Similarity	NPC216478
0.8113	Intermediate Similarity	NPC473154
0.8113	Intermediate Similarity	NPC474440

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 NPC119550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1242
0.2-0.3	3469
0.3-0.4	2637
0.4-0.5	1034
0.5-0.6	359
0.6-0.7	213
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD6686	Approved
0.7966	Intermediate Similarity	NPD8515	Approved
0.7966	Intermediate Similarity	NPD8517	Approved
0.7966	Intermediate Similarity	NPD8513	Phase 3
0.7966	Intermediate Similarity	NPD8516	Approved
0.7815	Intermediate Similarity	NPD7503	Approved
0.7788	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7507	Approved
0.7647	Intermediate Similarity	NPD7516	Approved
0.7615	Intermediate Similarity	NPD7638	Approved
0.7563	Intermediate Similarity	NPD7328	Approved
0.7563	Intermediate Similarity	NPD7327	Approved
0.7545	Intermediate Similarity	NPD7640	Approved
0.7545	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD8033	Approved
0.7521	Intermediate Similarity	NPD8133	Approved
0.752	Intermediate Similarity	NPD7319	Approved
0.7478	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6412	Phase 2
0.7455	Intermediate Similarity	NPD4225	Approved
0.7438	Intermediate Similarity	NPD8377	Approved
0.7438	Intermediate Similarity	NPD8294	Approved
0.7377	Intermediate Similarity	NPD8378	Approved
0.7377	Intermediate Similarity	NPD8380	Approved
0.7377	Intermediate Similarity	NPD8335	Approved
0.7377	Intermediate Similarity	NPD8379	Approved
0.7377	Intermediate Similarity	NPD8296	Approved
0.736	Intermediate Similarity	NPD8074	Phase 3
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5779	Approved
0.7315	Intermediate Similarity	NPD5778	Approved
0.7265	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8328	Phase 3
0.7203	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7115	Discovery
0.7177	Intermediate Similarity	NPD6370	Approved
0.7168	Intermediate Similarity	NPD5344	Discontinued
0.7165	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7838	Discovery
0.713	Intermediate Similarity	NPD46	Approved
0.713	Intermediate Similarity	NPD6698	Approved
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD6648	Approved
0.7064	Intermediate Similarity	NPD7637	Suspended
0.7064	Intermediate Similarity	NPD7983	Approved
0.7064	Intermediate Similarity	NPD6411	Approved
0.7063	Intermediate Similarity	NPD7492	Approved
0.7016	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD7632	Discontinued
0.6953	Remote Similarity	NPD7078	Approved
0.6911	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6101	Approved
0.688	Remote Similarity	NPD6319	Approved
0.688	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD8297	Approved
0.685	Remote Similarity	NPD6067	Discontinued
0.6825	Remote Similarity	NPD6016	Approved
0.6825	Remote Similarity	NPD6015	Approved
0.6822	Remote Similarity	NPD1694	Approved
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6803	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD6402	Approved
0.678	Remote Similarity	NPD5739	Approved
0.678	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6650	Approved
0.6777	Remote Similarity	NPD6649	Approved
0.6772	Remote Similarity	NPD5988	Approved
0.6757	Remote Similarity	NPD7515	Phase 2
0.6754	Remote Similarity	NPD7902	Approved
0.675	Remote Similarity	NPD6373	Approved
0.675	Remote Similarity	NPD6372	Approved
0.6723	Remote Similarity	NPD5697	Approved
0.6721	Remote Similarity	NPD6053	Discontinued
0.6697	Remote Similarity	NPD7524	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6008	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6617	Remote Similarity	NPD7260	Phase 2
0.6615	Remote Similarity	NPD8451	Approved
0.6612	Remote Similarity	NPD6014	Approved
0.6612	Remote Similarity	NPD6013	Approved
0.6612	Remote Similarity	NPD6012	Approved
0.6589	Remote Similarity	NPD7830	Approved
0.6589	Remote Similarity	NPD7829	Approved
0.6583	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4786	Approved
0.6565	Remote Similarity	NPD8448	Approved
0.6562	Remote Similarity	NPD6921	Approved
0.6562	Remote Similarity	NPD8444	Approved
0.6557	Remote Similarity	NPD6371	Approved
0.6545	Remote Similarity	NPD4251	Approved
0.6545	Remote Similarity	NPD4250	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3667	Approved
0.6529	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD8039	Approved
0.6491	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7900	Approved
0.6481	Remote Similarity	NPD6695	Phase 3
0.6466	Remote Similarity	NPD6083	Phase 2
0.6466	Remote Similarity	NPD6084	Phase 2
0.6462	Remote Similarity	NPD7604	Phase 2
0.646	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD6079	Approved
0.646	Remote Similarity	NPD8034	Phase 2
0.6455	Remote Similarity	NPD3618	Phase 1
0.6455	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD5328	Approved
0.6423	Remote Similarity	NPD4634	Approved
0.6418	Remote Similarity	NPD8390	Approved
0.6418	Remote Similarity	NPD8392	Approved
0.6418	Remote Similarity	NPD8391	Approved
0.6412	Remote Similarity	NPD8341	Approved
0.6412	Remote Similarity	NPD8299	Approved
0.6412	Remote Similarity	NPD8340	Approved
0.6412	Remote Similarity	NPD8342	Approved
0.6391	Remote Similarity	NPD6033	Approved
0.6387	Remote Similarity	NPD5211	Phase 2
0.6377	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD5285	Approved
0.6356	Remote Similarity	NPD5286	Approved
0.6356	Remote Similarity	NPD4696	Approved
0.6355	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8264	Approved
0.633	Remote Similarity	NPD7154	Phase 3
0.6328	Remote Similarity	NPD7641	Discontinued
0.6325	Remote Similarity	NPD4755	Approved
0.6324	Remote Similarity	NPD6845	Suspended
0.6316	Remote Similarity	NPD5284	Approved
0.6316	Remote Similarity	NPD5281	Approved
0.6306	Remote Similarity	NPD6684	Approved
0.6306	Remote Similarity	NPD7334	Approved
0.6306	Remote Similarity	NPD5330	Approved
0.6306	Remote Similarity	NPD6409	Approved
0.6306	Remote Similarity	NPD7521	Approved
0.6306	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD5695	Phase 3
0.6283	Remote Similarity	NPD6051	Approved
0.6281	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5141	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6262	Remote Similarity	NPD6929	Approved
0.6262	Remote Similarity	NPD7645	Phase 2
0.6261	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD7750	Discontinued
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD5222	Approved
0.6239	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5785	Approved
0.6226	Remote Similarity	NPD7799	Discontinued
0.6218	Remote Similarity	NPD4700	Approved
0.6207	Remote Similarity	NPD5282	Discontinued
0.6207	Remote Similarity	NPD7625	Phase 1
0.6204	Remote Similarity	NPD6930	Phase 2
0.6204	Remote Similarity	NPD7525	Registered
0.6204	Remote Similarity	NPD7332	Phase 2
0.6204	Remote Similarity	NPD4822	Approved
0.6204	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7514	Phase 3
0.6204	Remote Similarity	NPD4820	Approved
0.6204	Remote Similarity	NPD4821	Approved
0.6204	Remote Similarity	NPD4819	Approved
0.6204	Remote Similarity	NPD6931	Approved
0.6202	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD5174	Approved
0.6198	Remote Similarity	NPD5175	Approved
0.6195	Remote Similarity	NPD6903	Approved
0.6195	Remote Similarity	NPD6672	Approved
0.6195	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5737	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