NPASS Compound

Structure

NPC81567 OpenBabel07101719132D 37 39 0 0 1 0 0 0 0 0999 V2000 6.7611 1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2051 3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3608 5.4431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 2.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7055 -0.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7014 -0.5584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0195 -2.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3236 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8361 1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5164 3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 -0.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 2.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 2.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3608 4.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2986 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8611 0.0806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0027 0.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9732 -2.2745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 3.0056 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3280 1.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 1.5431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1724 0.0806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3280 4.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3966 0.8907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9697 0.1019 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8611 1.0556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1724 1.0556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9564 0.5716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6256 -2.9991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 -0.4069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 5.4431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3503 1.0934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2745 -1.3472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 3.9806 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 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 28 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 21 1 0 0 0 0 14 22 2 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 18 28 1 6 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 36 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 32 1 0 0 0 0 25 33 2 0 0 0 0 25 36 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 8 1 1 0 0 0 29 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.29
Volume:	538.974
LogP:	4.264
LogD:	3.484
LogS:	-4.407
# Rotatable Bonds:	11
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	5.744
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:	-4.772
MDCK Permeability:	0.00011610089131863788
Pgp-inhibitor:	0.996
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	90.1178970336914%
Volume Distribution (VD):	1.849
Pgp-substrate:	8.621020317077637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.459
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	4.043
Half-life (T1/2):	0.35

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.915
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.625
Carcinogencity:	0.691
Eye Corrosion:	0.052
Eye Irritation:	0.023
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: NPC81567

Natural Product ID:	NPC81567
*Common Name:**	Caseargrewins L
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] 3-methylbutanoate
Synonyms:	caseargrewins L
Standard InCHIKey:	HTPJIMISZAEBAL-MPACXXFOSA-N
Standard InCHI:	InChI=1S/C29H42O8/c1-9-17(4)10-11-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)12-16(2)3/h9-10,14,16,18,21,23-24,26-27,32H,1,11-13,15H2,2-8H3/b17-10-/t18-,21+,23+,24+,26+,27-,28-,29-/m1/s1
SMILES:	C=C/C(=CC[C@]1(C)[C@H](C)C[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:	CHEMBL415067
PubChem CID:	16756991
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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[548556]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	0.32	ug.mL-1	PMID[548556]

☑ 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 NPC81567 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	191
0.1-0.2	1003
0.2-0.3	3654
0.3-0.4	7252
0.4-0.5	13516
0.5-0.6	8114
0.6-0.7	6339
0.7-0.8	2455
0.8-0.85	80
0.85-0.9	9
0.9-0.95	43
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470321
1.0	High Similarity	NPC264867
1.0	High Similarity	NPC473207
1.0	High Similarity	NPC201880
0.9896	High Similarity	NPC475889
0.9896	High Similarity	NPC7644
0.9896	High Similarity	NPC7613
0.9896	High Similarity	NPC134270
0.9896	High Similarity	NPC127933
0.9796	High Similarity	NPC184512
0.9792	High Similarity	NPC238397
0.9792	High Similarity	NPC471363
0.9697	High Similarity	NPC311223
0.9694	High Similarity	NPC252296
0.96	High Similarity	NPC316974
0.9596	High Similarity	NPC88013
0.9596	High Similarity	NPC125423
0.9583	High Similarity	NPC473204
0.9505	High Similarity	NPC119550
0.95	High Similarity	NPC128795
0.95	High Similarity	NPC217921
0.95	High Similarity	NPC48548
0.95	High Similarity	NPC135015
0.9479	High Similarity	NPC471366
0.9479	High Similarity	NPC318917
0.9479	High Similarity	NPC472186
0.9479	High Similarity	NPC476800
0.9406	High Similarity	NPC40728
0.94	High Similarity	NPC109376
0.9381	High Similarity	NPC473545
0.9381	High Similarity	NPC472187
0.9375	High Similarity	NPC472188
0.9307	High Similarity	NPC470024
0.9307	High Similarity	NPC224660
0.93	High Similarity	NPC172867
0.93	High Similarity	NPC218158
0.9271	High Similarity	NPC171598
0.9175	High Similarity	NPC98112
0.9167	High Similarity	NPC471362
0.9167	High Similarity	NPC472189
0.9167	High Similarity	NPC471372
0.9126	High Similarity	NPC316708
0.9062	High Similarity	NPC88507
0.9038	High Similarity	NPC470026
0.9038	High Similarity	NPC17791
0.8952	High Similarity	NPC328074
0.8952	High Similarity	NPC317460
0.8952	High Similarity	NPC321272
0.8952	High Similarity	NPC470025
0.8878	High Similarity	NPC311166
0.8868	High Similarity	NPC470027
0.88	High Similarity	NPC477971
0.88	High Similarity	NPC477972
0.88	High Similarity	NPC161527
0.88	High Similarity	NPC477968
0.88	High Similarity	NPC219285
0.88	High Similarity	NPC20113
0.88	High Similarity	NPC228251
0.8646	High Similarity	NPC470819
0.8558	High Similarity	NPC82251
0.8557	High Similarity	NPC471370
0.8557	High Similarity	NPC471371
0.8557	High Similarity	NPC470817
0.8557	High Similarity	NPC469403
0.8544	High Similarity	NPC120009
0.8515	High Similarity	NPC474440
0.8515	High Similarity	NPC473154
0.85	High Similarity	NPC8954
0.85	High Similarity	NPC94905
0.8476	Intermediate Similarity	NPC475074
0.8476	Intermediate Similarity	NPC293512
0.8469	Intermediate Similarity	NPC477574
0.8462	Intermediate Similarity	NPC222161
0.84	Intermediate Similarity	NPC477969
0.84	Intermediate Similarity	NPC471786
0.84	Intermediate Similarity	NPC477970
0.84	Intermediate Similarity	NPC100892
0.84	Intermediate Similarity	NPC135224
0.84	Intermediate Similarity	NPC37603
0.8384	Intermediate Similarity	NPC99653
0.8381	Intermediate Similarity	NPC239961
0.8378	Intermediate Similarity	NPC473828
0.8378	Intermediate Similarity	NPC473617
0.8365	Intermediate Similarity	NPC471365
0.8365	Intermediate Similarity	NPC132395
0.8365	Intermediate Similarity	NPC471450
0.8365	Intermediate Similarity	NPC471364
0.8365	Intermediate Similarity	NPC45897
0.8351	Intermediate Similarity	NPC263079
0.835	Intermediate Similarity	NPC198992
0.835	Intermediate Similarity	NPC280991
0.8349	Intermediate Similarity	NPC293658
0.8349	Intermediate Similarity	NPC157441
0.8349	Intermediate Similarity	NPC474410
0.8349	Intermediate Similarity	NPC264153
0.8333	Intermediate Similarity	NPC41129
0.8318	Intermediate Similarity	NPC206618
0.8317	Intermediate Similarity	NPC165632
0.8304	Intermediate Similarity	NPC122971
0.8302	Intermediate Similarity	NPC472390
0.83	Intermediate Similarity	NPC189513
0.8286	Intermediate Similarity	NPC470768
0.8283	Intermediate Similarity	NPC124374
0.8269	Intermediate Similarity	NPC469606
0.8269	Intermediate Similarity	NPC273005
0.8269	Intermediate Similarity	NPC471889
0.8269	Intermediate Similarity	NPC470571
0.8269	Intermediate Similarity	NPC31058
0.8265	Intermediate Similarity	NPC261320
0.8257	Intermediate Similarity	NPC473125
0.8257	Intermediate Similarity	NPC194951
0.8257	Intermediate Similarity	NPC12046
0.8252	Intermediate Similarity	NPC324841
0.8241	Intermediate Similarity	NPC83005
0.8241	Intermediate Similarity	NPC177047
0.8235	Intermediate Similarity	NPC309503
0.8235	Intermediate Similarity	NPC155319
0.8235	Intermediate Similarity	NPC91197
0.8235	Intermediate Similarity	NPC239547
0.8235	Intermediate Similarity	NPC125551
0.8235	Intermediate Similarity	NPC96597
0.8224	Intermediate Similarity	NPC38948
0.8218	Intermediate Similarity	NPC13924
0.8218	Intermediate Similarity	NPC275310
0.8218	Intermediate Similarity	NPC230347
0.8218	Intermediate Similarity	NPC286612
0.8208	Intermediate Similarity	NPC470763
0.8208	Intermediate Similarity	NPC469607
0.8208	Intermediate Similarity	NPC470767
0.819	Intermediate Similarity	NPC23584
0.819	Intermediate Similarity	NPC471886
0.819	Intermediate Similarity	NPC471887
0.819	Intermediate Similarity	NPC471888
0.819	Intermediate Similarity	NPC471885
0.8182	Intermediate Similarity	NPC75167
0.8182	Intermediate Similarity	NPC48732
0.8182	Intermediate Similarity	NPC49413
0.8182	Intermediate Similarity	NPC220216
0.8182	Intermediate Similarity	NPC311592
0.8182	Intermediate Similarity	NPC44298
0.8182	Intermediate Similarity	NPC290608
0.8182	Intermediate Similarity	NPC473128
0.8182	Intermediate Similarity	NPC40133
0.8163	Intermediate Similarity	NPC69713
0.8155	Intermediate Similarity	NPC477928
0.8155	Intermediate Similarity	NPC216478
0.8142	Intermediate Similarity	NPC470914
0.8142	Intermediate Similarity	NPC477071
0.8137	Intermediate Similarity	NPC284194
0.8137	Intermediate Similarity	NPC471765
0.8137	Intermediate Similarity	NPC221801
0.8137	Intermediate Similarity	NPC211810
0.8125	Intermediate Similarity	NPC23046
0.8119	Intermediate Similarity	NPC470255
0.8119	Intermediate Similarity	NPC472360
0.8119	Intermediate Similarity	NPC472416
0.8108	Intermediate Similarity	NPC475163
0.8108	Intermediate Similarity	NPC181145
0.8095	Intermediate Similarity	NPC472552
0.8095	Intermediate Similarity	NPC121423
0.8095	Intermediate Similarity	NPC475344
0.8095	Intermediate Similarity	NPC11956
0.8095	Intermediate Similarity	NPC476471
0.8095	Intermediate Similarity	NPC300399
0.8095	Intermediate Similarity	NPC471482
0.8095	Intermediate Similarity	NPC37207
0.8091	Intermediate Similarity	NPC231797
0.8087	Intermediate Similarity	NPC471082
0.8081	Intermediate Similarity	NPC16265
0.8081	Intermediate Similarity	NPC246028
0.8061	Intermediate Similarity	NPC102640
0.8061	Intermediate Similarity	NPC471779
0.8058	Intermediate Similarity	NPC473244
0.8056	Intermediate Similarity	NPC325054
0.8041	Intermediate Similarity	NPC119001
0.8039	Intermediate Similarity	NPC276110
0.8037	Intermediate Similarity	NPC127609
0.8036	Intermediate Similarity	NPC207637
0.802	Intermediate Similarity	NPC162615
0.802	Intermediate Similarity	NPC152778
0.802	Intermediate Similarity	NPC472812
0.802	Intermediate Similarity	NPC205034
0.8019	Intermediate Similarity	NPC474124
0.8019	Intermediate Similarity	NPC281378
0.8018	Intermediate Similarity	NPC473159
0.8	Intermediate Similarity	NPC292196
0.8	Intermediate Similarity	NPC65034
0.8	Intermediate Similarity	NPC477717
0.8	Intermediate Similarity	NPC475617
0.8	Intermediate Similarity	NPC472554
0.8	Intermediate Similarity	NPC476204
0.8	Intermediate Similarity	NPC190837
0.8	Intermediate Similarity	NPC170084
0.8	Intermediate Similarity	NPC208189
0.7982	Intermediate Similarity	NPC31522
0.7982	Intermediate Similarity	NPC112457
0.7981	Intermediate Similarity	NPC278673
0.7965	Intermediate Similarity	NPC474483
0.7965	Intermediate Similarity	NPC203862
0.7965	Intermediate Similarity	NPC473405

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 NPC81567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1197
0.2-0.3	3569
0.3-0.4	2640
0.4-0.5	1023
0.5-0.6	318
0.6-0.7	220
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
0.789	Intermediate Similarity	NPD6686	Approved
0.7845	Intermediate Similarity	NPD7503	Approved
0.781	Intermediate Similarity	NPD7638	Approved
0.7736	Intermediate Similarity	NPD7639	Approved
0.7736	Intermediate Similarity	NPD7640	Approved
0.7692	Intermediate Similarity	NPD8513	Phase 3
0.7692	Intermediate Similarity	NPD8517	Approved
0.7692	Intermediate Similarity	NPD8515	Approved
0.7692	Intermediate Similarity	NPD8516	Approved
0.7586	Intermediate Similarity	NPD7328	Approved
0.7586	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD8033	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.7477	Intermediate Similarity	NPD4225	Approved
0.7458	Intermediate Similarity	NPD8294	Approved
0.7458	Intermediate Similarity	NPD8377	Approved
0.7438	Intermediate Similarity	NPD7507	Approved
0.7404	Intermediate Similarity	NPD7637	Suspended
0.7395	Intermediate Similarity	NPD8296	Approved
0.7395	Intermediate Similarity	NPD8380	Approved
0.7395	Intermediate Similarity	NPD8379	Approved
0.7395	Intermediate Similarity	NPD8335	Approved
0.7395	Intermediate Similarity	NPD8378	Approved
0.7345	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5778	Approved
0.7333	Intermediate Similarity	NPD5779	Approved
0.7315	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7319	Approved
0.7241	Intermediate Similarity	NPD8133	Approved
0.7228	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7117	Intermediate Similarity	NPD7632	Discontinued
0.7097	Intermediate Similarity	NPD8074	Phase 3
0.7091	Intermediate Similarity	NPD6648	Approved
0.7075	Intermediate Similarity	NPD6411	Approved
0.7059	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6370	Approved
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7736	Approved
0.7027	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD6399	Phase 3
0.6992	Remote Similarity	NPD8328	Phase 3
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6054	Approved
0.688	Remote Similarity	NPD6616	Approved
0.6827	Remote Similarity	NPD1694	Approved
0.6825	Remote Similarity	NPD7078	Approved
0.6822	Remote Similarity	NPD6698	Approved
0.6822	Remote Similarity	NPD46	Approved
0.681	Remote Similarity	NPD6899	Approved
0.681	Remote Similarity	NPD6881	Approved
0.6796	Remote Similarity	NPD6695	Phase 3
0.6789	Remote Similarity	NPD7748	Approved
0.6783	Remote Similarity	NPD5739	Approved
0.6783	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD6675	Approved
0.6783	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6650	Approved
0.678	Remote Similarity	NPD6649	Approved
0.6777	Remote Similarity	NPD6009	Approved
0.6759	Remote Similarity	NPD7515	Phase 2
0.6759	Remote Similarity	NPD7983	Approved
0.6757	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6748	Remote Similarity	NPD6059	Approved
0.6724	Remote Similarity	NPD5697	Approved
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6053	Discontinued
0.6723	Remote Similarity	NPD8297	Approved
0.672	Remote Similarity	NPD6067	Discontinued
0.6698	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD4251	Approved
0.6695	Remote Similarity	NPD6883	Approved
0.6695	Remote Similarity	NPD7290	Approved
0.6695	Remote Similarity	NPD7102	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD8264	Approved
0.664	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6638	Remote Similarity	NPD6008	Approved
0.6613	Remote Similarity	NPD6319	Approved
0.661	Remote Similarity	NPD6013	Approved
0.661	Remote Similarity	NPD6014	Approved
0.661	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD4249	Approved
0.6581	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD4786	Approved
0.6569	Remote Similarity	NPD6929	Approved
0.6569	Remote Similarity	NPD7645	Phase 2
0.6542	Remote Similarity	NPD7750	Discontinued
0.6542	Remote Similarity	NPD7524	Approved
0.6538	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3667	Approved
0.6529	Remote Similarity	NPD4632	Approved
0.6525	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD6931	Approved
0.6505	Remote Similarity	NPD6930	Phase 2
0.6505	Remote Similarity	NPD7332	Phase 2
0.6505	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7514	Phase 3
0.6505	Remote Similarity	NPD7525	Registered
0.65	Remote Similarity	NPD8039	Approved
0.6489	Remote Similarity	NPD7260	Phase 2
0.6486	Remote Similarity	NPD7900	Approved
0.6486	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7145	Approved
0.646	Remote Similarity	NPD6083	Phase 2
0.646	Remote Similarity	NPD6084	Phase 2
0.6455	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD8034	Phase 2
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD3618	Phase 1
0.6442	Remote Similarity	NPD6902	Approved
0.6429	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5328	Approved
0.6379	Remote Similarity	NPD5211	Phase 2
0.6373	Remote Similarity	NPD5776	Phase 2
0.6373	Remote Similarity	NPD6932	Approved
0.6373	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8451	Approved
0.6355	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5286	Approved
0.6348	Remote Similarity	NPD5285	Approved
0.6348	Remote Similarity	NPD4696	Approved
0.6346	Remote Similarity	NPD4819	Approved
0.6346	Remote Similarity	NPD4822	Approved
0.6346	Remote Similarity	NPD4821	Approved
0.6346	Remote Similarity	NPD4820	Approved
0.6337	Remote Similarity	NPD6942	Approved
0.6337	Remote Similarity	NPD7339	Approved
0.6328	Remote Similarity	NPD7829	Approved
0.6328	Remote Similarity	NPD7830	Approved
0.6328	Remote Similarity	NPD7604	Phase 2
0.6321	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD4755	Approved
0.6311	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD4271	Approved
0.6308	Remote Similarity	NPD8448	Approved
0.6306	Remote Similarity	NPD5281	Approved
0.6306	Remote Similarity	NPD5284	Approved
0.6306	Remote Similarity	NPD7087	Discontinued
0.6303	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD8444	Approved
0.6299	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD7146	Approved
0.6296	Remote Similarity	NPD6409	Approved
0.6296	Remote Similarity	NPD7334	Approved
0.6296	Remote Similarity	NPD5330	Approved
0.6296	Remote Similarity	NPD7521	Approved
0.6296	Remote Similarity	NPD6684	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6281	Remote Similarity	NPD6371	Approved
0.6275	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5141	Approved
0.627	Remote Similarity	NPD7101	Approved
0.627	Remote Similarity	NPD7100	Approved
0.626	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD5224	Approved
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6924	Approved
0.6238	Remote Similarity	NPD6926	Approved
0.6231	Remote Similarity	NPD6336	Discontinued
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5222	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5785	Approved
0.6207	Remote Similarity	NPD4700	Approved
0.6204	Remote Similarity	NPD6893	Approved
0.62	Remote Similarity	NPD7151	Approved
0.62	Remote Similarity	NPD7152	Approved
0.62	Remote Similarity	NPD7150	Approved
0.6195	Remote Similarity	NPD5282	Discontinued
0.6194	Remote Similarity	NPD6845	Suspended
0.619	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7509	Discontinued
0.619	Remote Similarity	NPD6335	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