NPASS Compound

Structure

NPC184512 OpenBabel07101718322D 38 40 0 0 1 0 0 0 0 0999 V2000 -3.8963 3.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7654 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7897 2.7461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7078 -0.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 -0.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0201 -2.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3507 1.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0514 4.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7897 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2065 3.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3616 4.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5167 3.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3263 1.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8385 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0180 -0.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3282 2.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0180 2.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3019 1.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8629 0.0807 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0039 0.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9744 -2.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 3.0075 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3282 1.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0180 1.5441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1731 0.0807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3282 4.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3968 0.8913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9703 0.1020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8629 1.0563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1731 1.0563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9582 0.5719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6272 -3.0009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3282 -0.4071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3282 5.4465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3511 1.0941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2759 -1.3481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 3.9831 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 6 21 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 26 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 23 2 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 19 29 1 6 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 32 2 0 0 0 0 21 36 1 0 0 0 0 22 37 1 6 0 0 0 23 27 1 0 0 0 0 24 29 1 1 0 0 0 24 30 1 0 0 0 0 25 30 1 6 0 0 0 25 33 1 0 0 0 0 26 34 2 0 0 0 0 26 37 1 0 0 0 0 27 35 1 6 0 0 0 27 38 1 0 0 0 0 28 30 1 6 0 0 0 28 36 1 0 0 0 0 28 38 1 0 0 0 0 29 7 1 1 0 0 0 30 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.3
Volume:	556.27
LogP:	4.645
LogD:	3.651
LogS:	-4.479
# Rotatable Bonds:	13
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	5.65
Fsp3:	0.7
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:	-4.745
MDCK Permeability:	8.722096390556544e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.407
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.399
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.333
Plasma Protein Binding (PPB):	93.89791107177734%
Volume Distribution (VD):	2.063
Pgp-substrate:	4.196747779846191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.184
CYP2C9-inhibitor:	0.546
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	4.197
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.965
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.639
Carcinogencity:	0.587
Eye Corrosion:	0.038
Eye Irritation:	0.019
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC184512

Natural Product ID:	NPC184512
*Common Name:**	Caseargrewins I
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-10-hydroxy-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 I
Standard InCHIKey:	OWZBTGIYKSYHIP-AHVFBGDZSA-N
Standard InCHI:	InChI=1S/C30H44O8/c1-8-10-11-12-26(34)37-22-16-23-27(35-20(5)31)38-28(36-21(6)32)30(23)24(17-22)29(7,14-13-18(3)9-2)19(4)15-25(30)33/h9,13,16,19,22,24-25,27-28,33H,2,8,10-12,14-15,17H2,1,3-7H3/b18-13-/t19-,22+,24+,25+,27+,28-,29-,30-/m1/s1
SMILES:	CCCCCC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)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:	CHEMBL398225
PubChem CID:	16756888
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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.04	ug.mL-1	PMID[479668]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	0.33	ug.mL-1	PMID[479668]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.36	ug.mL-1	PMID[479668]

☑ 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 NPC184512 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	994
0.2-0.3	3530
0.3-0.4	6650
0.4-0.5	13547
0.5-0.6	8070
0.6-0.7	6619
0.7-0.8	2909
0.8-0.85	86
0.85-0.9	25
0.9-0.95	39
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC252296
0.9796	High Similarity	NPC470321
0.9796	High Similarity	NPC473207
0.9796	High Similarity	NPC201880
0.9796	High Similarity	NPC264867
0.9796	High Similarity	NPC81567
0.9703	High Similarity	NPC119550
0.9694	High Similarity	NPC475889
0.9694	High Similarity	NPC134270
0.9694	High Similarity	NPC127933
0.9694	High Similarity	NPC7644
0.9694	High Similarity	NPC7613
0.9592	High Similarity	NPC471363
0.9592	High Similarity	NPC238397
0.9505	High Similarity	NPC311223
0.9412	High Similarity	NPC316974
0.9406	High Similarity	NPC125423
0.9406	High Similarity	NPC88013
0.9388	High Similarity	NPC473204
0.9314	High Similarity	NPC48548
0.9314	High Similarity	NPC128795
0.9314	High Similarity	NPC217921
0.9314	High Similarity	NPC135015
0.9286	High Similarity	NPC472186
0.9286	High Similarity	NPC471366
0.9286	High Similarity	NPC476800
0.9286	High Similarity	NPC318917
0.9223	High Similarity	NPC40728
0.9216	High Similarity	NPC109376
0.9192	High Similarity	NPC473545
0.9192	High Similarity	NPC472187
0.9184	High Similarity	NPC472188
0.9126	High Similarity	NPC470024
0.9126	High Similarity	NPC224660
0.9118	High Similarity	NPC172867
0.9118	High Similarity	NPC218158
0.9082	High Similarity	NPC171598
0.9082	High Similarity	NPC311166
0.899	High Similarity	NPC98112
0.898	High Similarity	NPC471372
0.898	High Similarity	NPC471362
0.898	High Similarity	NPC472189
0.8952	High Similarity	NPC316708
0.8878	High Similarity	NPC88507
0.8868	High Similarity	NPC470026
0.8868	High Similarity	NPC17791
0.8785	High Similarity	NPC328074
0.8785	High Similarity	NPC317460
0.8785	High Similarity	NPC470025
0.8785	High Similarity	NPC321272
0.8704	High Similarity	NPC470027
0.8667	High Similarity	NPC293512
0.8654	High Similarity	NPC222161
0.8627	High Similarity	NPC477972
0.8627	High Similarity	NPC477968
0.8627	High Similarity	NPC161527
0.8627	High Similarity	NPC219285
0.8627	High Similarity	NPC20113
0.8627	High Similarity	NPC477971
0.8627	High Similarity	NPC228251
0.8559	High Similarity	NPC473828
0.8559	High Similarity	NPC473617
0.8558	High Similarity	NPC471365
0.8558	High Similarity	NPC132395
0.8558	High Similarity	NPC471364
0.8532	High Similarity	NPC474410
0.8532	High Similarity	NPC157441
0.8532	High Similarity	NPC293658
0.8509	High Similarity	NPC41129
0.8482	Intermediate Similarity	NPC122971
0.8469	Intermediate Similarity	NPC470819
0.8462	Intermediate Similarity	NPC469606
0.8462	Intermediate Similarity	NPC31058
0.8462	Intermediate Similarity	NPC273005
0.844	Intermediate Similarity	NPC194951
0.844	Intermediate Similarity	NPC12046
0.8426	Intermediate Similarity	NPC83005
0.8396	Intermediate Similarity	NPC82251
0.8396	Intermediate Similarity	NPC469607
0.8384	Intermediate Similarity	NPC469403
0.8384	Intermediate Similarity	NPC471371
0.8384	Intermediate Similarity	NPC470817
0.8384	Intermediate Similarity	NPC471370
0.8381	Intermediate Similarity	NPC120009
0.8364	Intermediate Similarity	NPC311592
0.8364	Intermediate Similarity	NPC75167
0.835	Intermediate Similarity	NPC474440
0.835	Intermediate Similarity	NPC473154
0.835	Intermediate Similarity	NPC216478
0.8333	Intermediate Similarity	NPC94905
0.8333	Intermediate Similarity	NPC8954
0.8319	Intermediate Similarity	NPC477071
0.8318	Intermediate Similarity	NPC475074
0.8304	Intermediate Similarity	NPC23046
0.83	Intermediate Similarity	NPC477574
0.8288	Intermediate Similarity	NPC181145
0.8288	Intermediate Similarity	NPC475163
0.8241	Intermediate Similarity	NPC325054
0.8235	Intermediate Similarity	NPC37603
0.8235	Intermediate Similarity	NPC471786
0.8235	Intermediate Similarity	NPC477969
0.8235	Intermediate Similarity	NPC135224
0.8235	Intermediate Similarity	NPC477970
0.8235	Intermediate Similarity	NPC100892
0.8224	Intermediate Similarity	NPC239961
0.8224	Intermediate Similarity	NPC127609
0.8218	Intermediate Similarity	NPC99653
0.8208	Intermediate Similarity	NPC471450
0.8208	Intermediate Similarity	NPC45897
0.8198	Intermediate Similarity	NPC264153
0.819	Intermediate Similarity	NPC198992
0.819	Intermediate Similarity	NPC280991
0.8182	Intermediate Similarity	NPC263079
0.8182	Intermediate Similarity	NPC190837
0.8182	Intermediate Similarity	NPC292196
0.8174	Intermediate Similarity	NPC476204
0.8174	Intermediate Similarity	NPC170084
0.8165	Intermediate Similarity	NPC112457
0.8165	Intermediate Similarity	NPC206618
0.8165	Intermediate Similarity	NPC31522
0.8155	Intermediate Similarity	NPC165632
0.8148	Intermediate Similarity	NPC472390
0.8142	Intermediate Similarity	NPC473968
0.8142	Intermediate Similarity	NPC474483
0.8142	Intermediate Similarity	NPC473405
0.8137	Intermediate Similarity	NPC250075
0.8137	Intermediate Similarity	NPC189513
0.8131	Intermediate Similarity	NPC470768
0.8125	Intermediate Similarity	NPC472274
0.8125	Intermediate Similarity	NPC220293
0.8119	Intermediate Similarity	NPC124374
0.8113	Intermediate Similarity	NPC32577
0.8113	Intermediate Similarity	NPC471889
0.8113	Intermediate Similarity	NPC470571
0.8113	Intermediate Similarity	NPC114540
0.8113	Intermediate Similarity	NPC155332
0.8113	Intermediate Similarity	NPC476081
0.8108	Intermediate Similarity	NPC64106
0.8108	Intermediate Similarity	NPC161434
0.8108	Intermediate Similarity	NPC195132
0.8108	Intermediate Similarity	NPC125923
0.8108	Intermediate Similarity	NPC473125
0.8108	Intermediate Similarity	NPC65590
0.8108	Intermediate Similarity	NPC174836
0.8108	Intermediate Similarity	NPC212968
0.81	Intermediate Similarity	NPC261320
0.8095	Intermediate Similarity	NPC47024
0.8095	Intermediate Similarity	NPC324841
0.8091	Intermediate Similarity	NPC274507
0.8091	Intermediate Similarity	NPC127153
0.8091	Intermediate Similarity	NPC177047
0.8091	Intermediate Similarity	NPC235014
0.8091	Intermediate Similarity	NPC101450
0.8091	Intermediate Similarity	NPC129340
0.8087	Intermediate Similarity	NPC48692
0.8077	Intermediate Similarity	NPC91197
0.8077	Intermediate Similarity	NPC239547
0.8077	Intermediate Similarity	NPC309503
0.8077	Intermediate Similarity	NPC96597
0.8077	Intermediate Similarity	NPC155319
0.8077	Intermediate Similarity	NPC125551
0.8073	Intermediate Similarity	NPC300614
0.8073	Intermediate Similarity	NPC177524
0.8073	Intermediate Similarity	NPC38948
0.8073	Intermediate Similarity	NPC189075
0.8073	Intermediate Similarity	NPC219900
0.8073	Intermediate Similarity	NPC90946
0.8073	Intermediate Similarity	NPC392
0.8073	Intermediate Similarity	NPC275539
0.807	Intermediate Similarity	NPC471548
0.807	Intermediate Similarity	NPC45475
0.8058	Intermediate Similarity	NPC286612
0.8058	Intermediate Similarity	NPC13924
0.8058	Intermediate Similarity	NPC275310
0.8058	Intermediate Similarity	NPC230347
0.8056	Intermediate Similarity	NPC470763
0.8056	Intermediate Similarity	NPC34768
0.8056	Intermediate Similarity	NPC111952
0.8056	Intermediate Similarity	NPC470767
0.8053	Intermediate Similarity	NPC471816
0.8037	Intermediate Similarity	NPC471885
0.8037	Intermediate Similarity	NPC471886
0.8037	Intermediate Similarity	NPC23584
0.8037	Intermediate Similarity	NPC471888
0.8037	Intermediate Similarity	NPC36688
0.8037	Intermediate Similarity	NPC471887
0.8036	Intermediate Similarity	NPC44298
0.8036	Intermediate Similarity	NPC469463
0.8036	Intermediate Similarity	NPC40133
0.8036	Intermediate Similarity	NPC473128
0.8036	Intermediate Similarity	NPC290608
0.8036	Intermediate Similarity	NPC251309
0.8036	Intermediate Similarity	NPC49413
0.8036	Intermediate Similarity	NPC25909
0.8036	Intermediate Similarity	NPC469454
0.8036	Intermediate Similarity	NPC469496
0.802	Intermediate Similarity	NPC48732
0.802	Intermediate Similarity	NPC220216
0.8019	Intermediate Similarity	NPC154127
0.8018	Intermediate Similarity	NPC250481

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 NPC184512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1202
0.2-0.3	3440
0.3-0.4	2671
0.4-0.5	1076
0.5-0.6	318
0.6-0.7	247
0.7-0.8	33
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
0.8073	Intermediate Similarity	NPD6686	Approved
0.7863	Intermediate Similarity	NPD8513	Phase 3
0.7863	Intermediate Similarity	NPD8515	Approved
0.7863	Intermediate Similarity	NPD8517	Approved
0.7863	Intermediate Similarity	NPD8516	Approved
0.783	Intermediate Similarity	NPD7638	Approved
0.7757	Intermediate Similarity	NPD7640	Approved
0.7757	Intermediate Similarity	NPD7639	Approved
0.7712	Intermediate Similarity	NPD7503	Approved
0.7603	Intermediate Similarity	NPD7507	Approved
0.7524	Intermediate Similarity	NPD5778	Approved
0.7524	Intermediate Similarity	NPD5779	Approved
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7327	Approved
0.7458	Intermediate Similarity	NPD7328	Approved
0.7419	Intermediate Similarity	NPD7319	Approved
0.7417	Intermediate Similarity	NPD8033	Approved
0.7414	Intermediate Similarity	NPD8133	Approved
0.7395	Intermediate Similarity	NPD7516	Approved
0.7345	Intermediate Similarity	NPD6412	Phase 2
0.7339	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD8377	Approved
0.7333	Intermediate Similarity	NPD8294	Approved
0.7328	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8378	Approved
0.7273	Intermediate Similarity	NPD8380	Approved
0.7273	Intermediate Similarity	NPD8335	Approved
0.7273	Intermediate Similarity	NPD8379	Approved
0.7273	Intermediate Similarity	NPD8296	Approved
0.7264	Intermediate Similarity	NPD7637	Suspended
0.7264	Intermediate Similarity	NPD6411	Approved
0.7258	Intermediate Similarity	NPD8074	Phase 3
0.7227	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6370	Approved
0.72	Intermediate Similarity	NPD7736	Approved
0.7196	Intermediate Similarity	NPD6399	Phase 3
0.7182	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7097	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7115	Discovery
0.7075	Intermediate Similarity	NPD6101	Approved
0.7075	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6054	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7019	Intermediate Similarity	NPD1694	Approved
0.7009	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD46	Approved
0.7009	Intermediate Similarity	NPD7838	Discovery
0.6984	Remote Similarity	NPD7078	Approved
0.6983	Remote Similarity	NPD6899	Approved
0.6983	Remote Similarity	NPD6881	Approved
0.6972	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD6648	Approved
0.6957	Remote Similarity	NPD7128	Approved
0.6957	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD5739	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6944	Remote Similarity	NPD7983	Approved
0.6944	Remote Similarity	NPD7515	Phase 2
0.6942	Remote Similarity	NPD6009	Approved
0.6937	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6911	Remote Similarity	NPD6059	Approved
0.6903	Remote Similarity	NPD5344	Discontinued
0.6897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5697	Approved
0.6891	Remote Similarity	NPD8297	Approved
0.6891	Remote Similarity	NPD6053	Discontinued
0.688	Remote Similarity	NPD6067	Discontinued
0.6864	Remote Similarity	NPD7102	Approved
0.6864	Remote Similarity	NPD7290	Approved
0.6864	Remote Similarity	NPD6883	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6847	Remote Similarity	NPD7839	Suspended
0.6838	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7320	Approved
0.681	Remote Similarity	NPD6008	Approved
0.6807	Remote Similarity	NPD6617	Approved
0.6807	Remote Similarity	NPD6869	Approved
0.6807	Remote Similarity	NPD6847	Approved
0.6807	Remote Similarity	NPD8130	Phase 1
0.68	Remote Similarity	NPD5988	Approved
0.678	Remote Similarity	NPD6014	Approved
0.678	Remote Similarity	NPD6013	Approved
0.678	Remote Similarity	NPD6012	Approved
0.6774	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5701	Approved
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD4251	Approved
0.6729	Remote Similarity	NPD4250	Approved
0.67	Remote Similarity	NPD8039	Approved
0.6695	Remote Similarity	NPD6011	Approved
0.6694	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6641	Remote Similarity	NPD7260	Phase 2
0.6637	Remote Similarity	NPD6083	Phase 2
0.6637	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD8035	Phase 2
0.6636	Remote Similarity	NPD3618	Phase 1
0.6636	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD4249	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6607	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD5211	Phase 2
0.6542	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8264	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5285	Approved
0.6522	Remote Similarity	NPD5286	Approved
0.6522	Remote Similarity	NPD4696	Approved
0.6512	Remote Similarity	NPD8451	Approved
0.6509	Remote Similarity	NPD7154	Phase 3
0.6491	Remote Similarity	NPD4755	Approved
0.6486	Remote Similarity	NPD5284	Approved
0.6486	Remote Similarity	NPD5281	Approved
0.6484	Remote Similarity	NPD7604	Phase 2
0.6484	Remote Similarity	NPD7830	Approved
0.6484	Remote Similarity	NPD7829	Approved
0.6481	Remote Similarity	NPD7334	Approved
0.6481	Remote Similarity	NPD5330	Approved
0.6481	Remote Similarity	NPD7146	Approved
0.6481	Remote Similarity	NPD7521	Approved
0.6481	Remote Similarity	NPD6684	Approved
0.6481	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8448	Approved
0.646	Remote Similarity	NPD5695	Phase 3
0.6457	Remote Similarity	NPD8444	Approved
0.6457	Remote Similarity	NPD5983	Phase 2
0.6455	Remote Similarity	NPD6051	Approved
0.6446	Remote Similarity	NPD6371	Approved
0.6442	Remote Similarity	NPD7645	Phase 2
0.6442	Remote Similarity	NPD6929	Approved
0.6441	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD7101	Approved
0.6429	Remote Similarity	NPD7100	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.6422	Remote Similarity	NPD7524	Approved
0.6422	Remote Similarity	NPD7750	Discontinued
0.6412	Remote Similarity	NPD6033	Approved
0.641	Remote Similarity	NPD5224	Approved
0.641	Remote Similarity	NPD4633	Approved
0.641	Remote Similarity	NPD5225	Approved
0.641	Remote Similarity	NPD5226	Approved
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5221	Approved
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5785	Approved
0.6385	Remote Similarity	NPD6336	Discontinued
0.6381	Remote Similarity	NPD7514	Phase 3
0.6381	Remote Similarity	NPD7525	Registered
0.6381	Remote Similarity	NPD4820	Approved
0.6381	Remote Similarity	NPD6930	Phase 2
0.6381	Remote Similarity	NPD4821	Approved
0.6381	Remote Similarity	NPD7332	Phase 2
0.6381	Remote Similarity	NPD4819	Approved
0.6381	Remote Similarity	NPD6931	Approved
0.6381	Remote Similarity	NPD4822	Approved
0.6381	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4700	Approved
0.6372	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD6903	Approved
0.6356	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD5175	Approved
0.6355	Remote Similarity	NPD5362	Discontinued
0.6349	Remote Similarity	NPD6335	Approved
0.6348	Remote Similarity	NPD5173	Approved
0.6346	Remote Similarity	NPD4271	Approved
0.6346	Remote Similarity	NPD4268	Approved
0.6346	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7145	Approved
0.6343	Remote Similarity	NPD6845	Suspended
0.633	Remote Similarity	NPD5279	Phase 3
0.6328	Remote Similarity	NPD6921	Approved
0.6325	Remote Similarity	NPD5223	Approved
0.6321	Remote Similarity	NPD6902	Approved
0.632	Remote Similarity	NPD6868	Approved
0.632	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD8391	Approved
0.6316	Remote Similarity	NPD8390	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