NPASS Compound

Structure

NPC134270 OpenBabel07101718222D 34 36 0 0 1 0 0 0 0 0999 V2000 -2.2005 -3.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7471 -1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7741 -2.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6978 0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6201 2.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9985 -0.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3579 -4.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7741 -1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5153 -3.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3146 -1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8281 -1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0126 0.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0126 -2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2876 -1.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8552 -0.0804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9691 2.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1699 -2.9994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3273 -1.5399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0126 -1.5399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1699 -0.0804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3273 -4.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3957 -0.8889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9676 -0.1017 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8552 -1.0534 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1699 -1.0534 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0174 2.4721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 0.4060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -5.4318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3475 -1.0911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2697 1.3444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1699 -3.9723 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 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 31 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 17 26 1 1 0 0 0 18 28 2 0 0 0 0 18 32 1 0 0 0 0 19 33 1 1 0 0 0 20 24 1 0 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 30 2 0 0 0 0 23 33 1 0 0 0 0 24 31 1 1 0 0 0 24 34 1 0 0 0 0 25 27 1 1 0 0 0 25 32 1 0 0 0 0 25 34 1 0 0 0 0 26 6 1 6 0 0 0 27 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.28
Volume:	498.228
LogP:	4.039
LogD:	3.755
LogS:	-4.41
# Rotatable Bonds:	10
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.75
Fsp3:	0.704
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	6.5606516727712e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.751
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.385
Plasma Protein Binding (PPB):	92.09477996826172%
Volume Distribution (VD):	1.893
Pgp-substrate:	5.569751262664795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.528
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	4.891
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.743
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.678
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.507
Carcinogencity:	0.72
Eye Corrosion:	0.046
Eye Irritation:	0.029
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: NPC134270

Natural Product ID:	NPC134270
*Common Name:**	Caseargrewins G
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] butanoate
Synonyms:	caseargrewins G
Standard InCHIKey:	HYYVVSPRNZXNBO-MXRYFZCASA-N
Standard InCHI:	InChI=1S/C27H40O7/c1-8-10-23(30)33-19-14-20-24(31-7)34-25(32-18(5)28)27(20)21(15-19)26(6,12-11-16(3)9-2)17(4)13-22(27)29/h9,11,14,17,19,21-22,24-25,29H,2,8,10,12-13,15H2,1,3-7H3/b16-11-/t17-,19+,21+,22+,24+,25-,26-,27-/m1/s1
SMILES:	CCCC(=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:	CHEMBL231215
PubChem CID:	16756886
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	=	0.67	ug.mL-1	PMID[543100]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	5.57	ug.mL-1	PMID[543100]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.97	ug.mL-1	PMID[543100]

☑ 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 NPC134270 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	190
0.1-0.2	973
0.2-0.3	3682
0.3-0.4	7158
0.4-0.5	13605
0.5-0.6	8010
0.6-0.7	6639
0.7-0.8	2260
0.8-0.85	79
0.85-0.9	19
0.9-0.95	48
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC201880
0.9896	High Similarity	NPC81567
0.9896	High Similarity	NPC470321
0.9896	High Similarity	NPC473207
0.9896	High Similarity	NPC264867
0.9895	High Similarity	NPC238397
0.9895	High Similarity	NPC471363
0.9794	High Similarity	NPC252296
0.9792	High Similarity	NPC7644
0.9792	High Similarity	NPC127933
0.9792	High Similarity	NPC7613
0.9792	High Similarity	NPC475889
0.9694	High Similarity	NPC184512
0.9596	High Similarity	NPC311223
0.95	High Similarity	NPC316974
0.9495	High Similarity	NPC125423
0.9495	High Similarity	NPC88013
0.9479	High Similarity	NPC473204
0.9474	High Similarity	NPC472188
0.9406	High Similarity	NPC119550
0.94	High Similarity	NPC128795
0.94	High Similarity	NPC217921
0.94	High Similarity	NPC48548
0.94	High Similarity	NPC135015
0.9375	High Similarity	NPC318917
0.9375	High Similarity	NPC471366
0.9375	High Similarity	NPC472186
0.9375	High Similarity	NPC476800
0.9307	High Similarity	NPC40728
0.93	High Similarity	NPC109376
0.9278	High Similarity	NPC472187
0.9278	High Similarity	NPC473545
0.9271	High Similarity	NPC98112
0.9263	High Similarity	NPC471362
0.9263	High Similarity	NPC472189
0.9263	High Similarity	NPC471372
0.9208	High Similarity	NPC470024
0.9208	High Similarity	NPC224660
0.92	High Similarity	NPC218158
0.92	High Similarity	NPC172867
0.9167	High Similarity	NPC171598
0.9158	High Similarity	NPC88507
0.9029	High Similarity	NPC316708
0.8969	High Similarity	NPC311166
0.8942	High Similarity	NPC17791
0.8942	High Similarity	NPC470026
0.8889	High Similarity	NPC477972
0.8889	High Similarity	NPC477971
0.8889	High Similarity	NPC20113
0.8889	High Similarity	NPC161527
0.8889	High Similarity	NPC228251
0.8889	High Similarity	NPC219285
0.8889	High Similarity	NPC477968
0.8857	High Similarity	NPC317460
0.8857	High Similarity	NPC470025
0.8857	High Similarity	NPC321272
0.8857	High Similarity	NPC328074
0.8774	High Similarity	NPC470027
0.8737	High Similarity	NPC470819
0.8646	High Similarity	NPC471371
0.8646	High Similarity	NPC469403
0.8646	High Similarity	NPC471370
0.8646	High Similarity	NPC470817
0.8627	High Similarity	NPC120009
0.86	High Similarity	NPC474440
0.86	High Similarity	NPC473154
0.8586	High Similarity	NPC8954
0.8586	High Similarity	NPC94905
0.8558	High Similarity	NPC475074
0.8557	High Similarity	NPC477574
0.8544	High Similarity	NPC222161
0.8485	Intermediate Similarity	NPC135224
0.8485	Intermediate Similarity	NPC100892
0.8485	Intermediate Similarity	NPC477970
0.8485	Intermediate Similarity	NPC477969
0.8469	Intermediate Similarity	NPC99653
0.8462	Intermediate Similarity	NPC82251
0.8447	Intermediate Similarity	NPC132395
0.8447	Intermediate Similarity	NPC471364
0.8447	Intermediate Similarity	NPC471450
0.8447	Intermediate Similarity	NPC45897
0.8447	Intermediate Similarity	NPC471365
0.8438	Intermediate Similarity	NPC263079
0.8426	Intermediate Similarity	NPC157441
0.84	Intermediate Similarity	NPC165632
0.8396	Intermediate Similarity	NPC206618
0.8384	Intermediate Similarity	NPC189513
0.8381	Intermediate Similarity	NPC293512
0.8367	Intermediate Similarity	NPC124374
0.8351	Intermediate Similarity	NPC261320
0.835	Intermediate Similarity	NPC273005
0.835	Intermediate Similarity	NPC31058
0.835	Intermediate Similarity	NPC470571
0.835	Intermediate Similarity	NPC471889
0.835	Intermediate Similarity	NPC469606
0.8333	Intermediate Similarity	NPC194951
0.8333	Intermediate Similarity	NPC324841
0.8333	Intermediate Similarity	NPC12046
0.8317	Intermediate Similarity	NPC91197
0.8317	Intermediate Similarity	NPC96597
0.8317	Intermediate Similarity	NPC125551
0.8317	Intermediate Similarity	NPC239547
0.8317	Intermediate Similarity	NPC309503
0.8317	Intermediate Similarity	NPC155319
0.8302	Intermediate Similarity	NPC38948
0.83	Intermediate Similarity	NPC13924
0.83	Intermediate Similarity	NPC471786
0.83	Intermediate Similarity	NPC286612
0.83	Intermediate Similarity	NPC230347
0.83	Intermediate Similarity	NPC37603
0.83	Intermediate Similarity	NPC275310
0.8288	Intermediate Similarity	NPC473617
0.8288	Intermediate Similarity	NPC473828
0.8286	Intermediate Similarity	NPC239961
0.8286	Intermediate Similarity	NPC469607
0.8269	Intermediate Similarity	NPC471888
0.8269	Intermediate Similarity	NPC471886
0.8269	Intermediate Similarity	NPC471885
0.8269	Intermediate Similarity	NPC23584
0.8269	Intermediate Similarity	NPC471887
0.8265	Intermediate Similarity	NPC220216
0.8265	Intermediate Similarity	NPC48732
0.8257	Intermediate Similarity	NPC474410
0.8257	Intermediate Similarity	NPC264153
0.8257	Intermediate Similarity	NPC293658
0.8252	Intermediate Similarity	NPC280991
0.8252	Intermediate Similarity	NPC198992
0.8246	Intermediate Similarity	NPC41129
0.8235	Intermediate Similarity	NPC216478
0.8214	Intermediate Similarity	NPC122971
0.8208	Intermediate Similarity	NPC472390
0.82	Intermediate Similarity	NPC470255
0.8198	Intermediate Similarity	NPC23046
0.819	Intermediate Similarity	NPC470768
0.8182	Intermediate Similarity	NPC475163
0.8173	Intermediate Similarity	NPC11956
0.8173	Intermediate Similarity	NPC37207
0.8173	Intermediate Similarity	NPC471482
0.8173	Intermediate Similarity	NPC300399
0.8165	Intermediate Similarity	NPC473125
0.8163	Intermediate Similarity	NPC246028
0.8163	Intermediate Similarity	NPC16265
0.8148	Intermediate Similarity	NPC83005
0.8148	Intermediate Similarity	NPC177047
0.8144	Intermediate Similarity	NPC471779
0.8131	Intermediate Similarity	NPC325054
0.8125	Intermediate Similarity	NPC119001
0.8119	Intermediate Similarity	NPC276110
0.8113	Intermediate Similarity	NPC470767
0.8113	Intermediate Similarity	NPC127609
0.8113	Intermediate Similarity	NPC470763
0.81	Intermediate Similarity	NPC162615
0.81	Intermediate Similarity	NPC205034
0.81	Intermediate Similarity	NPC472812
0.81	Intermediate Similarity	NPC152778
0.8091	Intermediate Similarity	NPC44298
0.8091	Intermediate Similarity	NPC473128
0.8091	Intermediate Similarity	NPC290608
0.8091	Intermediate Similarity	NPC49413
0.8091	Intermediate Similarity	NPC40133
0.8091	Intermediate Similarity	NPC75167
0.8091	Intermediate Similarity	NPC311592
0.8077	Intermediate Similarity	NPC475617
0.8073	Intermediate Similarity	NPC208189
0.8073	Intermediate Similarity	NPC65034
0.8061	Intermediate Similarity	NPC69713
0.8058	Intermediate Similarity	NPC477928
0.8058	Intermediate Similarity	NPC278673
0.8056	Intermediate Similarity	NPC31522
0.8056	Intermediate Similarity	NPC112457
0.8053	Intermediate Similarity	NPC477071
0.8053	Intermediate Similarity	NPC470914
0.8039	Intermediate Similarity	NPC221801
0.8039	Intermediate Similarity	NPC284194
0.8039	Intermediate Similarity	NPC211810
0.8039	Intermediate Similarity	NPC471765
0.8039	Intermediate Similarity	NPC16967
0.8021	Intermediate Similarity	NPC471367
0.802	Intermediate Similarity	NPC104925
0.802	Intermediate Similarity	NPC298973
0.802	Intermediate Similarity	NPC96736
0.802	Intermediate Similarity	NPC211238
0.802	Intermediate Similarity	NPC472416
0.802	Intermediate Similarity	NPC250075
0.802	Intermediate Similarity	NPC105490
0.802	Intermediate Similarity	NPC57117
0.802	Intermediate Similarity	NPC472360
0.802	Intermediate Similarity	NPC178949
0.8019	Intermediate Similarity	NPC85593
0.8019	Intermediate Similarity	NPC31430
0.8018	Intermediate Similarity	NPC181145
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC32577
0.8	Intermediate Similarity	NPC472815
0.8	Intermediate Similarity	NPC155332
0.8	Intermediate Similarity	NPC475344
0.8	Intermediate Similarity	NPC472552
0.8	Intermediate Similarity	NPC471082
0.8	Intermediate Similarity	NPC231797
0.8	Intermediate Similarity	NPC476471

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 NPC134270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1177
0.2-0.3	3544
0.3-0.4	2658
0.4-0.5	1046
0.5-0.6	317
0.6-0.7	227
0.7-0.8	24
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
0.7885	Intermediate Similarity	NPD7638	Approved
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD6686	Approved
0.7759	Intermediate Similarity	NPD7503	Approved
0.7607	Intermediate Similarity	NPD8513	Phase 3
0.7607	Intermediate Similarity	NPD8517	Approved
0.7607	Intermediate Similarity	NPD8515	Approved
0.7607	Intermediate Similarity	NPD8516	Approved
0.7547	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.7476	Intermediate Similarity	NPD7637	Suspended
0.7458	Intermediate Similarity	NPD8033	Approved
0.7436	Intermediate Similarity	NPD7516	Approved
0.7404	Intermediate Similarity	NPD5779	Approved
0.7404	Intermediate Similarity	NPD5778	Approved
0.7373	Intermediate Similarity	NPD8294	Approved
0.7373	Intermediate Similarity	NPD8377	Approved
0.7355	Intermediate Similarity	NPD7507	Approved
0.7311	Intermediate Similarity	NPD8379	Approved
0.7311	Intermediate Similarity	NPD8296	Approved
0.7311	Intermediate Similarity	NPD8380	Approved
0.7311	Intermediate Similarity	NPD8335	Approved
0.7311	Intermediate Similarity	NPD8378	Approved
0.73	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7222	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7632	Discontinued
0.7177	Intermediate Similarity	NPD7319	Approved
0.7156	Intermediate Similarity	NPD6648	Approved
0.7155	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7107	Intermediate Similarity	NPD6370	Approved
0.7105	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7736	Approved
0.7091	Intermediate Similarity	NPD5344	Discontinued
0.7075	Intermediate Similarity	NPD6399	Phase 3
0.7069	Intermediate Similarity	NPD6882	Approved
0.7048	Intermediate Similarity	NPD7838	Discovery
0.7016	Intermediate Similarity	NPD8074	Phase 3
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD7492	Approved
0.6975	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7115	Discovery
0.6961	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6101	Approved
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6054	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.6911	Remote Similarity	NPD8328	Phase 3
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1694	Approved
0.688	Remote Similarity	NPD7078	Approved
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.6863	Remote Similarity	NPD6695	Phase 3
0.6852	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD5739	Approved
0.6842	Remote Similarity	NPD6675	Approved
0.6842	Remote Similarity	NPD6402	Approved
0.6842	Remote Similarity	NPD7128	Approved
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6009	Approved
0.6822	Remote Similarity	NPD7515	Phase 2
0.6818	Remote Similarity	NPD7902	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.6783	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD6053	Discontinued
0.6774	Remote Similarity	NPD6067	Discontinued
0.6762	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD4250	Approved
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6748	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6735	Remote Similarity	NPD8264	Approved
0.6729	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD6698	Approved
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD6650	Approved
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD6649	Approved
0.6695	Remote Similarity	NPD8130	Phase 1
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD8297	Approved
0.6638	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD6051	Approved
0.6635	Remote Similarity	NPD4786	Approved
0.6634	Remote Similarity	NPD7645	Phase 2
0.6634	Remote Similarity	NPD6929	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6604	Remote Similarity	NPD7750	Discontinued
0.6602	Remote Similarity	NPD3667	Approved
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4632	Approved
0.6581	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD7839	Suspended
0.6569	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7525	Registered
0.6569	Remote Similarity	NPD7514	Phase 3
0.6569	Remote Similarity	NPD7332	Phase 2
0.6569	Remote Similarity	NPD6930	Phase 2
0.6569	Remote Similarity	NPD6931	Approved
0.6566	Remote Similarity	NPD8039	Approved
0.6545	Remote Similarity	NPD7900	Approved
0.6545	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7145	Approved
0.6532	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD6083	Phase 2
0.6518	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD8034	Phase 2
0.6514	Remote Similarity	NPD6079	Approved
0.6509	Remote Similarity	NPD3618	Phase 1
0.6505	Remote Similarity	NPD6902	Approved
0.6486	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5328	Approved
0.6436	Remote Similarity	NPD6932	Approved
0.6436	Remote Similarity	NPD6925	Approved
0.6436	Remote Similarity	NPD5776	Phase 2
0.6435	Remote Similarity	NPD5211	Phase 2
0.6417	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7260	Phase 2
0.6408	Remote Similarity	NPD4820	Approved
0.6408	Remote Similarity	NPD4819	Approved
0.6408	Remote Similarity	NPD4821	Approved
0.6408	Remote Similarity	NPD4822	Approved
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD6942	Approved
0.64	Remote Similarity	NPD7339	Approved
0.6381	Remote Similarity	NPD7154	Phase 3
0.6378	Remote Similarity	NPD7604	Phase 2
0.6373	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD4271	Approved
0.6372	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD6409	Approved
0.6355	Remote Similarity	NPD5330	Approved
0.6355	Remote Similarity	NPD7146	Approved
0.6355	Remote Similarity	NPD6684	Approved
0.6355	Remote Similarity	NPD7521	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6339	Remote Similarity	NPD5695	Phase 3
0.6337	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6371	Approved
0.6325	Remote Similarity	NPD5141	Approved
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6308	Remote Similarity	NPD6033	Approved
0.6306	Remote Similarity	NPD4202	Approved
0.63	Remote Similarity	NPD6926	Approved
0.63	Remote Similarity	NPD6924	Approved
0.6296	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5226	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6283	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5222	Approved
0.6283	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD6336	Discontinued
0.6279	Remote Similarity	NPD8451	Approved
0.6273	Remote Similarity	NPD5785	Approved
0.6263	Remote Similarity	NPD7151	Approved
0.6263	Remote Similarity	NPD7152	Approved
0.6263	Remote Similarity	NPD7150	Approved
0.6262	Remote Similarity	NPD6893	Approved
0.6261	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6335	Approved
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD6672	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6239	Remote Similarity	NPD7513	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