NPASS Compound

Structure

NPC311223 OpenBabel07101718282D 38 40 0 0 1 0 0 0 0 0999 V2000 6.9345 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 5.5827 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 -1.7450 -0.5727 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 5.9345 1.0827 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 -0.5296 4.0827 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 -1.3956 4.5827 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 -2.0540 0.3783 0.0000 C 0 0 0 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 -3.0322 0.5862 0.0000 O 0 0 0 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 9 2 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 28 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 6 0 0 0 18 30 2 0 0 0 0 18 35 1 0 0 0 0 19 31 2 0 0 0 0 19 36 1 0 0 0 0 20 37 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 32 2 0 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 29 1 6 0 0 0 25 34 1 0 0 0 0 26 35 1 6 0 0 0 26 38 1 0 0 0 0 27 29 1 6 0 0 0 27 36 1 0 0 0 0 27 38 1 0 0 0 0 28 8 1 1 0 0 0 29 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.28
Volume:	547.764
LogP:	3.827
LogD:	2.42
LogS:	-4.371
# Rotatable Bonds:	11
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	5.888
Fsp3:	0.69
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:	-4.886
MDCK Permeability:	0.0001748751092236489
Pgp-inhibitor:	0.991
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.785

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	85.68668365478516%
Volume Distribution (VD):	1.449
Pgp-substrate:	13.143977165222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.184
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	3.178
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.468
Carcinogencity:	0.727
Eye Corrosion:	0.007
Eye Irritation:	0.012
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC311223

Natural Product ID:	NPC311223
*Common Name:**	Esculentin B
IUPAC Name:	[(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-9,10-dihydroxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 3-methylbutanoate
Synonyms:
Standard InCHIKey:	LPSTZZWXOOHMOA-OZUCLCINSA-N
Standard InCHI:	InChI=1S/C29H42O9/c1-9-16(4)10-11-28(8)17(5)24(33)25(34)29-21(26(35-18(6)30)38-27(29)36-19(7)31)13-20(14-22(28)29)37-23(32)12-15(2)3/h9-10,13,15,17,20,22,24-27,33-34H,1,11-12,14H2,2-8H3/b16-10-/t17-,20+,22+,24-,25+,26+,27-,28-,29-/m1/s1
SMILES:	C=C/C(=CC[C@]1(C)[C@H](C)[C@@H](O)[C@@H]([C@@]23[C@H]1C[C@@H](OC(=O)CC(C)C)C=C3[C@H](O[C@H]2OC(=O)C)OC(=O)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL413790
PubChem CID:	44425427
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	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	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	=	0.68	ug.mL-1	PMID[508856]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.17	ug.mL-1	PMID[508856]

☑ 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 NPC311223 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	195
0.1-0.2	1040
0.2-0.3	3756
0.3-0.4	6853
0.4-0.5	13361
0.5-0.6	8578
0.6-0.7	6050
0.7-0.8	2685
0.8-0.85	88
0.85-0.9	15
0.9-0.95	44
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC316974
0.9899	High Similarity	NPC125423
0.9899	High Similarity	NPC88013
0.9802	High Similarity	NPC119550
0.98	High Similarity	NPC128795
0.98	High Similarity	NPC217921
0.98	High Similarity	NPC48548
0.98	High Similarity	NPC135015
0.9703	High Similarity	NPC40728
0.9697	High Similarity	NPC201880
0.9697	High Similarity	NPC470321
0.9697	High Similarity	NPC264867
0.9697	High Similarity	NPC473207
0.9697	High Similarity	NPC81567
0.9596	High Similarity	NPC7644
0.9596	High Similarity	NPC134270
0.9596	High Similarity	NPC127933
0.9596	High Similarity	NPC475889
0.9596	High Similarity	NPC7613
0.9505	High Similarity	NPC184512
0.9495	High Similarity	NPC238397
0.9495	High Similarity	NPC471363
0.9417	High Similarity	NPC316708
0.9406	High Similarity	NPC252296
0.9327	High Similarity	NPC470026
0.9293	High Similarity	NPC473204
0.9238	High Similarity	NPC328074
0.9238	High Similarity	NPC317460
0.9238	High Similarity	NPC321272
0.9238	High Similarity	NPC470025
0.9192	High Similarity	NPC471366
0.9192	High Similarity	NPC476800
0.9192	High Similarity	NPC472186
0.9192	High Similarity	NPC318917
0.9151	High Similarity	NPC470027
0.9143	High Similarity	NPC17791
0.9126	High Similarity	NPC109376
0.91	High Similarity	NPC473545
0.91	High Similarity	NPC472187
0.9091	High Similarity	NPC472188
0.9038	High Similarity	NPC224660
0.9038	High Similarity	NPC470024
0.9029	High Similarity	NPC218158
0.9029	High Similarity	NPC172867
0.899	High Similarity	NPC171598
0.89	High Similarity	NPC98112
0.8889	High Similarity	NPC471362
0.8889	High Similarity	NPC471372
0.8889	High Similarity	NPC472189
0.8788	High Similarity	NPC88507
0.8667	High Similarity	NPC82251
0.8614	High Similarity	NPC311166
0.8585	High Similarity	NPC293512
0.8571	High Similarity	NPC122971
0.8544	High Similarity	NPC477971
0.8544	High Similarity	NPC477972
0.8544	High Similarity	NPC219285
0.8544	High Similarity	NPC161527
0.8544	High Similarity	NPC228251
0.8544	High Similarity	NPC477968
0.8544	High Similarity	NPC20113
0.8519	High Similarity	NPC177047
0.8491	Intermediate Similarity	NPC239961
0.8482	Intermediate Similarity	NPC473828
0.8482	Intermediate Similarity	NPC473617
0.8476	Intermediate Similarity	NPC23584
0.8462	Intermediate Similarity	NPC280991
0.8462	Intermediate Similarity	NPC198992
0.8455	Intermediate Similarity	NPC264153
0.8455	Intermediate Similarity	NPC474410
0.8455	Intermediate Similarity	NPC293658
0.8435	Intermediate Similarity	NPC41129
0.8426	Intermediate Similarity	NPC206618
0.8411	Intermediate Similarity	NPC472390
0.8407	Intermediate Similarity	NPC470914
0.8396	Intermediate Similarity	NPC470768
0.8384	Intermediate Similarity	NPC470819
0.8381	Intermediate Similarity	NPC11956
0.8381	Intermediate Similarity	NPC472552
0.8381	Intermediate Similarity	NPC470571
0.8364	Intermediate Similarity	NPC473125
0.835	Intermediate Similarity	NPC239547
0.835	Intermediate Similarity	NPC309503
0.835	Intermediate Similarity	NPC91197
0.835	Intermediate Similarity	NPC125551
0.835	Intermediate Similarity	NPC96597
0.835	Intermediate Similarity	NPC155319
0.8349	Intermediate Similarity	NPC83005
0.8333	Intermediate Similarity	NPC275310
0.8333	Intermediate Similarity	NPC38948
0.8333	Intermediate Similarity	NPC230347
0.8333	Intermediate Similarity	NPC286612
0.8318	Intermediate Similarity	NPC470767
0.8318	Intermediate Similarity	NPC470763
0.8302	Intermediate Similarity	NPC120009
0.8302	Intermediate Similarity	NPC281378
0.8302	Intermediate Similarity	NPC474124
0.83	Intermediate Similarity	NPC469403
0.83	Intermediate Similarity	NPC471371
0.83	Intermediate Similarity	NPC471370
0.83	Intermediate Similarity	NPC470817
0.8288	Intermediate Similarity	NPC290608
0.8288	Intermediate Similarity	NPC49413
0.8288	Intermediate Similarity	NPC44298
0.8288	Intermediate Similarity	NPC473128
0.8288	Intermediate Similarity	NPC75167
0.8288	Intermediate Similarity	NPC40133
0.8288	Intermediate Similarity	NPC311592
0.8286	Intermediate Similarity	NPC472554
0.8286	Intermediate Similarity	NPC475617
0.8269	Intermediate Similarity	NPC477928
0.8269	Intermediate Similarity	NPC474440
0.8269	Intermediate Similarity	NPC473154
0.8252	Intermediate Similarity	NPC8954
0.8252	Intermediate Similarity	NPC94905
0.8246	Intermediate Similarity	NPC477071
0.8241	Intermediate Similarity	NPC475074
0.823	Intermediate Similarity	NPC23046
0.823	Intermediate Similarity	NPC473405
0.823	Intermediate Similarity	NPC473968
0.8224	Intermediate Similarity	NPC222161
0.8218	Intermediate Similarity	NPC477574
0.8214	Intermediate Similarity	NPC181145
0.8214	Intermediate Similarity	NPC475163
0.8208	Intermediate Similarity	NPC476471
0.8208	Intermediate Similarity	NPC475344
0.8208	Intermediate Similarity	NPC121423
0.8198	Intermediate Similarity	NPC212968
0.8198	Intermediate Similarity	NPC64106
0.8198	Intermediate Similarity	NPC125923
0.8198	Intermediate Similarity	NPC65590
0.8198	Intermediate Similarity	NPC231797
0.819	Intermediate Similarity	NPC188968
0.819	Intermediate Similarity	NPC272223
0.819	Intermediate Similarity	NPC471082
0.8158	Intermediate Similarity	NPC471548
0.8155	Intermediate Similarity	NPC477970
0.8155	Intermediate Similarity	NPC477969
0.8155	Intermediate Similarity	NPC37603
0.8155	Intermediate Similarity	NPC135224
0.8155	Intermediate Similarity	NPC471786
0.8155	Intermediate Similarity	NPC100892
0.8142	Intermediate Similarity	NPC207637
0.8142	Intermediate Similarity	NPC471816
0.8137	Intermediate Similarity	NPC99653
0.8131	Intermediate Similarity	NPC132395
0.8131	Intermediate Similarity	NPC471365
0.8131	Intermediate Similarity	NPC471364
0.8131	Intermediate Similarity	NPC471450
0.8131	Intermediate Similarity	NPC45897
0.8125	Intermediate Similarity	NPC157441
0.8125	Intermediate Similarity	NPC473159
0.8108	Intermediate Similarity	NPC208189
0.8108	Intermediate Similarity	NPC250481
0.8108	Intermediate Similarity	NPC190837
0.8108	Intermediate Similarity	NPC285410
0.8108	Intermediate Similarity	NPC292196
0.8108	Intermediate Similarity	NPC263827
0.8108	Intermediate Similarity	NPC65034
0.8103	Intermediate Similarity	NPC476204
0.8103	Intermediate Similarity	NPC170084
0.8103	Intermediate Similarity	NPC233500
0.81	Intermediate Similarity	NPC263079
0.8091	Intermediate Similarity	NPC472534
0.8091	Intermediate Similarity	NPC143706
0.8091	Intermediate Similarity	NPC257853
0.8087	Intermediate Similarity	NPC475775
0.8087	Intermediate Similarity	NPC219656
0.8087	Intermediate Similarity	NPC476529
0.8077	Intermediate Similarity	NPC165632
0.8077	Intermediate Similarity	NPC221801
0.8077	Intermediate Similarity	NPC284194
0.8077	Intermediate Similarity	NPC211810
0.8077	Intermediate Similarity	NPC471765
0.8073	Intermediate Similarity	NPC33053
0.8073	Intermediate Similarity	NPC473586
0.807	Intermediate Similarity	NPC203862
0.807	Intermediate Similarity	NPC474483
0.8067	Intermediate Similarity	NPC470780
0.8058	Intermediate Similarity	NPC472360
0.8058	Intermediate Similarity	NPC211238
0.8058	Intermediate Similarity	NPC189513
0.8058	Intermediate Similarity	NPC472416
0.8058	Intermediate Similarity	NPC178949
0.8058	Intermediate Similarity	NPC96736
0.8056	Intermediate Similarity	NPC475585
0.8056	Intermediate Similarity	NPC85593
0.8056	Intermediate Similarity	NPC474550
0.8056	Intermediate Similarity	NPC473543
0.8056	Intermediate Similarity	NPC93352
0.8056	Intermediate Similarity	NPC31430
0.8056	Intermediate Similarity	NPC473577
0.8053	Intermediate Similarity	NPC469877
0.8053	Intermediate Similarity	NPC470919
0.8053	Intermediate Similarity	NPC472274
0.8053	Intermediate Similarity	NPC220293
0.8039	Intermediate Similarity	NPC124374
0.8037	Intermediate Similarity	NPC472815
0.8037	Intermediate Similarity	NPC471889
0.8037	Intermediate Similarity	NPC201191

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 NPC311223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1251
0.2-0.3	3560
0.3-0.4	2636
0.4-0.5	983
0.5-0.6	332
0.6-0.7	199
0.7-0.8	25
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
0.8	Intermediate Similarity	NPD6686	Approved
0.7949	Intermediate Similarity	NPD7503	Approved
0.7797	Intermediate Similarity	NPD8517	Approved
0.7797	Intermediate Similarity	NPD8515	Approved
0.7797	Intermediate Similarity	NPD8513	Phase 3
0.7797	Intermediate Similarity	NPD8516	Approved
0.7778	Intermediate Similarity	NPD7516	Approved
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.7647	Intermediate Similarity	NPD8033	Approved
0.7611	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7563	Intermediate Similarity	NPD8294	Approved
0.7563	Intermediate Similarity	NPD8377	Approved
0.7541	Intermediate Similarity	NPD7507	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.736	Intermediate Similarity	NPD7319	Approved
0.735	Intermediate Similarity	NPD8133	Approved
0.7304	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5344	Discontinued
0.7281	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7838	Discovery
0.7207	Intermediate Similarity	NPD6648	Approved
0.72	Intermediate Similarity	NPD8074	Phase 3
0.7196	Intermediate Similarity	NPD7637	Suspended
0.7167	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5779	Approved
0.713	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD8328	Phase 3
0.7094	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7115	Discovery
0.7019	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6370	Approved
0.7008	Intermediate Similarity	NPD7736	Approved
0.6975	Remote Similarity	NPD6882	Approved
0.6944	Remote Similarity	NPD6698	Approved
0.6944	Remote Similarity	NPD46	Approved
0.693	Remote Similarity	NPD7632	Discontinued
0.6929	Remote Similarity	NPD8293	Discontinued
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7492	Approved
0.6881	Remote Similarity	NPD7983	Approved
0.6881	Remote Similarity	NPD6411	Approved
0.6855	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7524	Approved
0.6818	Remote Similarity	NPD6399	Phase 3
0.6797	Remote Similarity	NPD7078	Approved
0.6748	Remote Similarity	NPD6009	Approved
0.672	Remote Similarity	NPD6319	Approved
0.672	Remote Similarity	NPD6059	Approved
0.6698	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD8297	Approved
0.6693	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6636	Remote Similarity	NPD1694	Approved
0.6614	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6649	Approved
0.6612	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.661	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD7748	Approved
0.6604	Remote Similarity	NPD6695	Phase 3
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6579	Remote Similarity	NPD7902	Approved
0.6577	Remote Similarity	NPD7515	Phase 2
0.6557	Remote Similarity	NPD6053	Discontinued
0.6555	Remote Similarity	NPD5697	Approved
0.6529	Remote Similarity	NPD6883	Approved
0.6529	Remote Similarity	NPD7290	Approved
0.6529	Remote Similarity	NPD7102	Approved
0.6514	Remote Similarity	NPD4251	Approved
0.6514	Remote Similarity	NPD4250	Approved
0.65	Remote Similarity	NPD7320	Approved
0.6491	Remote Similarity	NPD7839	Suspended
0.6475	Remote Similarity	NPD6869	Approved
0.6475	Remote Similarity	NPD6617	Approved
0.6475	Remote Similarity	NPD6847	Approved
0.6475	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD8264	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6466	Remote Similarity	NPD7260	Phase 2
0.6462	Remote Similarity	NPD8451	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6446	Remote Similarity	NPD6014	Approved
0.6434	Remote Similarity	NPD7829	Approved
0.6434	Remote Similarity	NPD7830	Approved
0.6422	Remote Similarity	NPD4249	Approved
0.6417	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5701	Approved
0.6412	Remote Similarity	NPD8448	Approved
0.6406	Remote Similarity	NPD8444	Approved
0.6406	Remote Similarity	NPD6921	Approved
0.6396	Remote Similarity	NPD6051	Approved
0.6393	Remote Similarity	NPD6371	Approved
0.6389	Remote Similarity	NPD4786	Approved
0.6381	Remote Similarity	NPD6929	Approved
0.6381	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD7750	Discontinued
0.6355	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3667	Approved
0.6321	Remote Similarity	NPD7525	Registered
0.6321	Remote Similarity	NPD7332	Phase 2
0.6321	Remote Similarity	NPD7514	Phase 3
0.6321	Remote Similarity	NPD6931	Approved
0.6321	Remote Similarity	NPD6930	Phase 2
0.6321	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8039	Approved
0.6308	Remote Similarity	NPD7604	Phase 2
0.6294	Remote Similarity	NPD7625	Phase 1
0.6293	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6084	Phase 2
0.6286	Remote Similarity	NPD7145	Approved
0.6283	Remote Similarity	NPD6079	Approved
0.6283	Remote Similarity	NPD8035	Phase 2
0.6283	Remote Similarity	NPD8034	Phase 2
0.6279	Remote Similarity	NPD5983	Phase 2
0.6273	Remote Similarity	NPD3618	Phase 1
0.6269	Remote Similarity	NPD8390	Approved
0.6269	Remote Similarity	NPD8392	Approved
0.6269	Remote Similarity	NPD8391	Approved
0.6262	Remote Similarity	NPD6902	Approved
0.6261	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8299	Approved
0.626	Remote Similarity	NPD4634	Approved
0.626	Remote Similarity	NPD8342	Approved
0.626	Remote Similarity	NPD8341	Approved
0.626	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6241	Remote Similarity	NPD6033	Approved
0.6232	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5126	Approved
0.6231	Remote Similarity	NPD5125	Phase 3
0.6218	Remote Similarity	NPD5211	Phase 2
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3168	Discontinued
0.619	Remote Similarity	NPD5776	Phase 2
0.619	Remote Similarity	NPD6925	Approved
0.619	Remote Similarity	NPD6932	Approved
0.6186	Remote Similarity	NPD5286	Approved
0.6186	Remote Similarity	NPD5285	Approved
0.6186	Remote Similarity	NPD4696	Approved
0.6182	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6845	Suspended
0.6172	Remote Similarity	NPD7641	Discontinued
0.6168	Remote Similarity	NPD4820	Approved
0.6168	Remote Similarity	NPD4819	Approved
0.6168	Remote Similarity	NPD4821	Approved
0.6168	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.6154	Remote Similarity	NPD6942	Approved
0.6147	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7154	Phase 3
0.6147	Remote Similarity	NPD3669	Approved
0.614	Remote Similarity	NPD5281	Approved
0.614	Remote Similarity	NPD7087	Discontinued
0.614	Remote Similarity	NPD5284	Approved
0.6134	Remote Similarity	NPD4159	Approved
0.6132	Remote Similarity	NPD4268	Approved
0.6132	Remote Similarity	NPD4271	Approved
0.6126	Remote Similarity	NPD7146	Approved
0.6126	Remote Similarity	NPD7334	Approved
0.6126	Remote Similarity	NPD6409	Approved
0.6126	Remote Similarity	NPD7521	Approved
0.6126	Remote Similarity	NPD5330	Approved
0.6126	Remote Similarity	NPD6684	Approved
0.6124	Remote Similarity	NPD7100	Approved
0.6124	Remote Similarity	NPD7101	Approved
0.6121	Remote Similarity	NPD5695	Phase 3
0.6116	Remote Similarity	NPD5141	Approved
0.6116	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7799	Discontinued
0.6095	Remote Similarity	NPD3701	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data