NPASS Compound

Structure

NPC252296 OpenBabel07101719252D 36 38 0 0 1 0 0 0 0 0999 V2000 -3.8913 3.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7567 1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7823 2.7426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7031 -0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0188 -2.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3464 1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0013 0.3686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0475 4.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7823 1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2037 3.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3599 4.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 3.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3208 1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8336 1.0549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 -0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 2.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 2.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2951 1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8592 0.0806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9719 -2.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 3.0036 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3278 1.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 1.5421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1716 0.0806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3278 4.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 0.8901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9690 0.1018 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8592 1.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1716 1.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6238 -2.9971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 -0.4066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3278 5.4395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3494 1.0927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2730 -1.3463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 3.9780 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 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 7 33 1 0 0 0 0 8 10 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 19 28 1 6 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 35 1 6 0 0 0 22 26 1 0 0 0 0 23 28 1 1 0 0 0 23 29 1 0 0 0 0 24 29 1 6 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 33 1 6 0 0 0 26 36 1 0 0 0 0 27 29 1 6 0 0 0 27 34 1 0 0 0 0 27 36 1 0 0 0 0 28 6 1 1 0 0 0 29 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.31
Volume:	532.82
LogP:	4.734
LogD:	4.087
LogS:	-4.703
# Rotatable Bonds:	12
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.672
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:	-4.702
MDCK Permeability:	4.731286026071757e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.763
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	95.92623138427734%
Volume Distribution (VD):	2.082
Pgp-substrate:	2.798018217086792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.459
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	5.753
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.759
AMES Toxicity:	0.478
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.52
Carcinogencity:	0.654
Eye Corrosion:	0.033
Eye Irritation:	0.024
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC252296

Natural Product ID:	NPC252296
*Common Name:**	Caseargrewins J
IUPAC Name:	[(1S,3S,5R,6aS,7R,8R,10S,10aS)-1-acetyloxy-10-hydroxy-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 J
Standard InCHIKey:	LNLATCNMZQLNMH-JHAOYEHPSA-N
Standard InCHI:	InChI=1S/C29H44O7/c1-8-10-11-12-25(32)35-21-16-22-26(33-7)36-27(34-20(5)30)29(22)23(17-21)28(6,14-13-18(3)9-2)19(4)15-24(29)31/h9,13,16,19,21,23-24,26-27,31H,2,8,10-12,14-15,17H2,1,3-7H3/b18-13-/t19-,21+,23+,24+,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]3O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL231314
PubChem CID:	16756889
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	=	1.22	ug.mL-1	PMID[548394]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.99	ug.mL-1	PMID[548394]

☑ 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 NPC252296 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	194
0.1-0.2	974
0.2-0.3	3517
0.3-0.4	6549
0.4-0.5	13749
0.5-0.6	7966
0.6-0.7	6795
0.7-0.8	2759
0.8-0.85	93
0.85-0.9	26
0.9-0.95	43
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC184512
0.9794	High Similarity	NPC134270
0.9694	High Similarity	NPC201880
0.9694	High Similarity	NPC470321
0.9694	High Similarity	NPC264867
0.9694	High Similarity	NPC473207
0.9694	High Similarity	NPC81567
0.9691	High Similarity	NPC471363
0.9691	High Similarity	NPC238397
0.9604	High Similarity	NPC119550
0.9592	High Similarity	NPC7644
0.9592	High Similarity	NPC127933
0.9592	High Similarity	NPC475889
0.9592	High Similarity	NPC7613
0.9406	High Similarity	NPC311223
0.9314	High Similarity	NPC316974
0.9307	High Similarity	NPC88013
0.9307	High Similarity	NPC125423
0.9286	High Similarity	NPC473204
0.9278	High Similarity	NPC472188
0.9216	High Similarity	NPC217921
0.9216	High Similarity	NPC128795
0.9216	High Similarity	NPC135015
0.9216	High Similarity	NPC48548
0.9184	High Similarity	NPC476800
0.9184	High Similarity	NPC318917
0.9184	High Similarity	NPC472186
0.9184	High Similarity	NPC471366
0.9175	High Similarity	NPC311166
0.9126	High Similarity	NPC40728
0.9118	High Similarity	NPC109376
0.9091	High Similarity	NPC472187
0.9091	High Similarity	NPC473545
0.9082	High Similarity	NPC98112
0.9072	High Similarity	NPC471372
0.9072	High Similarity	NPC471362
0.9072	High Similarity	NPC472189
0.9029	High Similarity	NPC224660
0.9029	High Similarity	NPC470024
0.902	High Similarity	NPC172867
0.902	High Similarity	NPC218158
0.898	High Similarity	NPC171598
0.8969	High Similarity	NPC88507
0.8857	High Similarity	NPC316708
0.8774	High Similarity	NPC470026
0.8774	High Similarity	NPC17791
0.8738	High Similarity	NPC222161
0.8713	High Similarity	NPC477972
0.8713	High Similarity	NPC219285
0.8713	High Similarity	NPC228251
0.8713	High Similarity	NPC161527
0.8713	High Similarity	NPC477971
0.8713	High Similarity	NPC477968
0.8713	High Similarity	NPC20113
0.8692	High Similarity	NPC321272
0.8692	High Similarity	NPC470025
0.8692	High Similarity	NPC317460
0.8692	High Similarity	NPC328074
0.8641	High Similarity	NPC471364
0.8641	High Similarity	NPC132395
0.8641	High Similarity	NPC471365
0.8611	High Similarity	NPC470027
0.8611	High Similarity	NPC157441
0.8571	High Similarity	NPC293512
0.8557	High Similarity	NPC470819
0.8544	High Similarity	NPC469606
0.8544	High Similarity	NPC31058
0.8544	High Similarity	NPC273005
0.8519	High Similarity	NPC194951
0.8519	High Similarity	NPC12046
0.8476	Intermediate Similarity	NPC469607
0.8469	Intermediate Similarity	NPC471371
0.8469	Intermediate Similarity	NPC470817
0.8469	Intermediate Similarity	NPC469403
0.8469	Intermediate Similarity	NPC471370
0.8468	Intermediate Similarity	NPC473617
0.8468	Intermediate Similarity	NPC473828
0.8462	Intermediate Similarity	NPC120009
0.844	Intermediate Similarity	NPC474410
0.844	Intermediate Similarity	NPC293658
0.8431	Intermediate Similarity	NPC473154
0.8431	Intermediate Similarity	NPC216478
0.8431	Intermediate Similarity	NPC474440
0.8421	Intermediate Similarity	NPC41129
0.8416	Intermediate Similarity	NPC94905
0.8416	Intermediate Similarity	NPC8954
0.8396	Intermediate Similarity	NPC475074
0.8393	Intermediate Similarity	NPC122971
0.8384	Intermediate Similarity	NPC477574
0.8378	Intermediate Similarity	NPC23046
0.8364	Intermediate Similarity	NPC475163
0.8333	Intermediate Similarity	NPC83005
0.8318	Intermediate Similarity	NPC325054
0.8317	Intermediate Similarity	NPC477969
0.8317	Intermediate Similarity	NPC100892
0.8317	Intermediate Similarity	NPC135224
0.8317	Intermediate Similarity	NPC477970
0.8302	Intermediate Similarity	NPC127609
0.8302	Intermediate Similarity	NPC82251
0.83	Intermediate Similarity	NPC99653
0.8286	Intermediate Similarity	NPC471450
0.8286	Intermediate Similarity	NPC45897
0.8273	Intermediate Similarity	NPC311592
0.8273	Intermediate Similarity	NPC75167
0.8265	Intermediate Similarity	NPC263079
0.8241	Intermediate Similarity	NPC112457
0.8241	Intermediate Similarity	NPC31522
0.8241	Intermediate Similarity	NPC206618
0.8235	Intermediate Similarity	NPC165632
0.823	Intermediate Similarity	NPC477071
0.8218	Intermediate Similarity	NPC189513
0.8218	Intermediate Similarity	NPC250075
0.82	Intermediate Similarity	NPC124374
0.8198	Intermediate Similarity	NPC181145
0.819	Intermediate Similarity	NPC470571
0.819	Intermediate Similarity	NPC155332
0.819	Intermediate Similarity	NPC114540
0.819	Intermediate Similarity	NPC476081
0.819	Intermediate Similarity	NPC32577
0.819	Intermediate Similarity	NPC471889
0.8182	Intermediate Similarity	NPC261320
0.8173	Intermediate Similarity	NPC47024
0.8173	Intermediate Similarity	NPC324841
0.8165	Intermediate Similarity	NPC235014
0.8165	Intermediate Similarity	NPC101450
0.8155	Intermediate Similarity	NPC91197
0.8155	Intermediate Similarity	NPC309503
0.8155	Intermediate Similarity	NPC155319
0.8155	Intermediate Similarity	NPC96597
0.8155	Intermediate Similarity	NPC125551
0.8155	Intermediate Similarity	NPC239547
0.8148	Intermediate Similarity	NPC90946
0.8148	Intermediate Similarity	NPC38948
0.8148	Intermediate Similarity	NPC275539
0.8148	Intermediate Similarity	NPC189075
0.8148	Intermediate Similarity	NPC300614
0.8137	Intermediate Similarity	NPC286612
0.8137	Intermediate Similarity	NPC230347
0.8137	Intermediate Similarity	NPC37603
0.8137	Intermediate Similarity	NPC13924
0.8137	Intermediate Similarity	NPC471786
0.8137	Intermediate Similarity	NPC275310
0.8131	Intermediate Similarity	NPC34768
0.8131	Intermediate Similarity	NPC239961
0.8125	Intermediate Similarity	NPC471816
0.8113	Intermediate Similarity	NPC471887
0.8113	Intermediate Similarity	NPC471888
0.8113	Intermediate Similarity	NPC471886
0.8113	Intermediate Similarity	NPC471885
0.8113	Intermediate Similarity	NPC23584
0.8113	Intermediate Similarity	NPC36688
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC264153
0.81	Intermediate Similarity	NPC220216
0.81	Intermediate Similarity	NPC48732
0.8095	Intermediate Similarity	NPC280991
0.8095	Intermediate Similarity	NPC198992
0.8091	Intermediate Similarity	NPC190837
0.8091	Intermediate Similarity	NPC292196
0.8087	Intermediate Similarity	NPC170084
0.8087	Intermediate Similarity	NPC476204
0.8081	Intermediate Similarity	NPC477128
0.8073	Intermediate Similarity	NPC5475
0.8073	Intermediate Similarity	NPC472216
0.8073	Intermediate Similarity	NPC284828
0.8073	Intermediate Similarity	NPC472534
0.8073	Intermediate Similarity	NPC173905
0.8073	Intermediate Similarity	NPC476759
0.8073	Intermediate Similarity	NPC143706
0.8058	Intermediate Similarity	NPC112654
0.8058	Intermediate Similarity	NPC284518
0.8056	Intermediate Similarity	NPC302788
0.8056	Intermediate Similarity	NPC472390
0.8056	Intermediate Similarity	NPC110496
0.8053	Intermediate Similarity	NPC473968
0.8053	Intermediate Similarity	NPC473405
0.8053	Intermediate Similarity	NPC474483
0.8039	Intermediate Similarity	NPC477130
0.8039	Intermediate Similarity	NPC470255
0.8039	Intermediate Similarity	NPC477129
0.8039	Intermediate Similarity	NPC474554
0.8037	Intermediate Similarity	NPC239162
0.8037	Intermediate Similarity	NPC470768
0.8036	Intermediate Similarity	NPC472274
0.8036	Intermediate Similarity	NPC220293
0.802	Intermediate Similarity	NPC233345
0.802	Intermediate Similarity	NPC474631
0.802	Intermediate Similarity	NPC186363
0.8019	Intermediate Similarity	NPC37207
0.8019	Intermediate Similarity	NPC300399
0.8019	Intermediate Similarity	NPC134077
0.8019	Intermediate Similarity	NPC165250
0.8019	Intermediate Similarity	NPC11956
0.8019	Intermediate Similarity	NPC471482
0.8019	Intermediate Similarity	NPC478156
0.8019	Intermediate Similarity	NPC58329
0.8018	Intermediate Similarity	NPC473125
0.8018	Intermediate Similarity	NPC212968

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 NPC252296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1173
0.2-0.3	3443
0.3-0.4	2676
0.4-0.5	1086
0.5-0.6	323
0.6-0.7	255
0.7-0.8	32
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
0.7982	Intermediate Similarity	NPD6686	Approved
0.7905	Intermediate Similarity	NPD7638	Approved
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7778	Intermediate Similarity	NPD8516	Approved
0.7778	Intermediate Similarity	NPD8513	Phase 3
0.7778	Intermediate Similarity	NPD8515	Approved
0.7778	Intermediate Similarity	NPD8517	Approved
0.7627	Intermediate Similarity	NPD7503	Approved
0.7596	Intermediate Similarity	NPD5779	Approved
0.7596	Intermediate Similarity	NPD5778	Approved
0.7521	Intermediate Similarity	NPD7507	Approved
0.7434	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD4225	Approved
0.7373	Intermediate Similarity	NPD7328	Approved
0.7373	Intermediate Similarity	NPD7327	Approved
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD8033	Approved
0.7333	Intermediate Similarity	NPD7637	Suspended
0.7328	Intermediate Similarity	NPD8133	Approved
0.7311	Intermediate Similarity	NPD7516	Approved
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6370	Approved
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7258	Intermediate Similarity	NPD7736	Approved
0.725	Intermediate Similarity	NPD8377	Approved
0.725	Intermediate Similarity	NPD8294	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7207	Intermediate Similarity	NPD7632	Discontinued
0.719	Intermediate Similarity	NPD8380	Approved
0.719	Intermediate Similarity	NPD8379	Approved
0.719	Intermediate Similarity	NPD8335	Approved
0.719	Intermediate Similarity	NPD8378	Approved
0.719	Intermediate Similarity	NPD8296	Approved
0.7177	Intermediate Similarity	NPD8074	Phase 3
0.7177	Intermediate Similarity	NPD8293	Discontinued
0.7157	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6054	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7091	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1694	Approved
0.7073	Intermediate Similarity	NPD8328	Phase 3
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD7078	Approved
0.7037	Intermediate Similarity	NPD7748	Approved
0.7027	Intermediate Similarity	NPD6648	Approved
0.7018	Intermediate Similarity	NPD7128	Approved
0.7018	Intermediate Similarity	NPD5739	Approved
0.7018	Intermediate Similarity	NPD6675	Approved
0.7018	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6964	Remote Similarity	NPD5344	Discontinued
0.6957	Remote Similarity	NPD5697	Approved
0.6949	Remote Similarity	NPD6053	Discontinued
0.6935	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7838	Discovery
0.6916	Remote Similarity	NPD6698	Approved
0.6916	Remote Similarity	NPD46	Approved
0.6911	Remote Similarity	NPD6016	Approved
0.6911	Remote Similarity	NPD6015	Approved
0.6897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7320	Approved
0.687	Remote Similarity	NPD6008	Approved
0.6864	Remote Similarity	NPD6649	Approved
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD8130	Phase 1
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6650	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD5988	Approved
0.6852	Remote Similarity	NPD7983	Approved
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD6373	Approved
0.6838	Remote Similarity	NPD6014	Approved
0.6838	Remote Similarity	NPD6372	Approved
0.6838	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD4786	Approved
0.6827	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5701	Approved
0.6807	Remote Similarity	NPD8297	Approved
0.6796	Remote Similarity	NPD3667	Approved
0.6796	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4250	Approved
0.6792	Remote Similarity	NPD4251	Approved
0.6768	Remote Similarity	NPD8039	Approved
0.6757	Remote Similarity	NPD7839	Suspended
0.6752	Remote Similarity	NPD6011	Approved
0.675	Remote Similarity	NPD4632	Approved
0.6731	Remote Similarity	NPD6695	Phase 3
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4249	Approved
0.6698	Remote Similarity	NPD3618	Phase 1
0.6697	Remote Similarity	NPD8035	Phase 2
0.6697	Remote Similarity	NPD8034	Phase 2
0.6697	Remote Similarity	NPD6079	Approved
0.6696	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8264	Approved
0.6583	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5286	Approved
0.6579	Remote Similarity	NPD5285	Approved
0.6579	Remote Similarity	NPD4696	Approved
0.6571	Remote Similarity	NPD7154	Phase 3
0.6565	Remote Similarity	NPD7260	Phase 2
0.6549	Remote Similarity	NPD4755	Approved
0.6545	Remote Similarity	NPD5284	Approved
0.6545	Remote Similarity	NPD5281	Approved
0.6542	Remote Similarity	NPD7334	Approved
0.6542	Remote Similarity	NPD6409	Approved
0.6542	Remote Similarity	NPD7521	Approved
0.6542	Remote Similarity	NPD6684	Approved
0.6542	Remote Similarity	NPD5330	Approved
0.6542	Remote Similarity	NPD7146	Approved
0.6535	Remote Similarity	NPD7604	Phase 2
0.6518	Remote Similarity	NPD5695	Phase 3
0.6514	Remote Similarity	NPD6051	Approved
0.6508	Remote Similarity	NPD5983	Phase 2
0.6505	Remote Similarity	NPD6929	Approved
0.6505	Remote Similarity	NPD7645	Phase 2
0.65	Remote Similarity	NPD6371	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6486	Remote Similarity	NPD4202	Approved
0.6481	Remote Similarity	NPD7750	Discontinued
0.6481	Remote Similarity	NPD7524	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6466	Remote Similarity	NPD5225	Approved
0.6466	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD4633	Approved
0.6466	Remote Similarity	NPD5226	Approved
0.6462	Remote Similarity	NPD6033	Approved
0.646	Remote Similarity	NPD5221	Approved
0.646	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5222	Approved
0.6455	Remote Similarity	NPD5785	Approved
0.6442	Remote Similarity	NPD7514	Phase 3
0.6442	Remote Similarity	NPD4821	Approved
0.6442	Remote Similarity	NPD4822	Approved
0.6442	Remote Similarity	NPD6930	Phase 2
0.6442	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6931	Approved
0.6442	Remote Similarity	NPD7525	Registered
0.6442	Remote Similarity	NPD7332	Phase 2
0.6442	Remote Similarity	NPD4819	Approved
0.6442	Remote Similarity	NPD4820	Approved
0.6435	Remote Similarity	NPD4700	Approved
0.6434	Remote Similarity	NPD8451	Approved
0.6434	Remote Similarity	NPD6336	Discontinued
0.6429	Remote Similarity	NPD5282	Discontinued
0.6422	Remote Similarity	NPD5737	Approved
0.6422	Remote Similarity	NPD6903	Approved
0.6422	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6672	Approved
0.6415	Remote Similarity	NPD5362	Discontinued
0.641	Remote Similarity	NPD5175	Approved
0.641	Remote Similarity	NPD5174	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7145	Approved
0.6408	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD4268	Approved
0.6406	Remote Similarity	NPD7829	Approved
0.6406	Remote Similarity	NPD7830	Approved
0.6404	Remote Similarity	NPD5173	Approved
0.64	Remote Similarity	NPD6335	Approved
0.6389	Remote Similarity	NPD5279	Phase 3
0.6387	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8448	Approved
0.6381	Remote Similarity	NPD6902	Approved
0.6379	Remote Similarity	NPD5223	Approved
0.6378	Remote Similarity	NPD8444	Approved
0.6372	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6274	Approved
0.6371	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3133	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