NPASS Compound

Structure

NPC470854 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 2.3505 1.1964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2882 2.1867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6088 -0.8764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7855 0.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 1.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 0.5531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4514 -0.2146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2332 0.6830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1922 1.1430 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3217 -0.2337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4415 0.4265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0082 -0.0847 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2692 -0.5517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8070 1.3978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8991 0.3641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8862 -0.2880 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6715 -1.1200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4210 -0.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9926 1.6202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0755 -0.7814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3341 -0.7280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2274 -1.4826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7580 -1.7025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4339 0.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 0.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 18 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 20 1 0 0 0 0 6 19 1 0 0 0 0 6 28 1 0 0 0 0 7 10 1 0 0 0 0 8 14 1 0 0 0 0 8 21 2 0 0 0 0 9 22 2 0 0 0 0 9 29 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 1 0 0 0 11 16 1 0 0 0 0 11 23 1 6 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 1 0 0 0 13 17 1 1 0 0 0 13 19 1 0 0 0 0 14 17 1 1 0 0 0 14 25 1 0 0 0 0 15 18 1 6 0 0 0 15 26 1 0 0 0 0 16 19 1 6 0 0 0 16 29 1 0 0 0 0 17 2 1 1 0 0 0 18 20 1 1 0 0 0 18 28 1 0 0 0 0 19 20 1 6 0 0 0 20 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.16
Volume:	382.897
LogP:	-0.054
LogD:	-0.187
LogS:	-3.704
# Rotatable Bonds:	0
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	6.799
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.774
MDCK Permeability:	8.013819751795381e-05
Pgp-inhibitor:	0.149
Pgp-substrate:	0.931
Human Intestinal Absorption (HIA):	0.816
20% Bioavailability (F20%):	0.67
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	28.683507919311523%
Volume Distribution (VD):	0.321
Pgp-substrate:	60.07266616821289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	2.479
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.485
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.287
Carcinogencity:	0.531
Eye Corrosion:	0.004
Eye Irritation:	0.011
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: NPC470854

Natural Product ID:	NPC470854
*Common Name:**	Indaquassin C
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WPPVOFUTBNIYFS-QCAWFNPZSA-N
Standard InCHI:	InChI=1S/C20H26O9/c1-7-4-8(21)14(25)17(2)10(7)11(23)16-19-6-28-18(3,15(26)12(24)13(17)19)20(19,27)5-9(22)29-16/h4,10-16,23-27H,5-6H2,1-3H3/t10-,11-,12-,13-,14-,15+,16-,17+,18+,19+,20-/m1/s1
SMILES:	O=C1O[C@@H]2[C@H](O)[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]42[C@](C1)(O)[C@@](C)(OC4)[C@H]([C@@H]3O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270645
PubChem CID:	76330544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	10.5	%	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	204.0	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	340.8	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	117.6	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	81.6	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	91.2	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	TIME	=	55.2	hr	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	62.5	%	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	48.9	%	PMID[546170]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	47.6	%	PMID[546170]

☑ 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 NPC470854 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	247
0.1-0.2	1455
0.2-0.3	4488
0.3-0.4	7668
0.4-0.5	11610
0.5-0.6	7610
0.6-0.7	5441
0.7-0.8	3509
0.8-0.85	498
0.85-0.9	99
0.9-0.95	51
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122033
1.0	High Similarity	NPC287343
1.0	High Similarity	NPC474654
1.0	High Similarity	NPC97908
0.9725	High Similarity	NPC204552
0.9725	High Similarity	NPC188667
0.9725	High Similarity	NPC17772
0.972	High Similarity	NPC49451
0.972	High Similarity	NPC7921
0.972	High Similarity	NPC208998
0.964	High Similarity	NPC102822
0.964	High Similarity	NPC477046
0.955	High Similarity	NPC112038
0.9545	High Similarity	NPC251310
0.9541	High Similarity	NPC251236
0.9541	High Similarity	NPC96312
0.9541	High Similarity	NPC40632
0.9541	High Similarity	NPC328374
0.9533	High Similarity	NPC146945
0.9533	High Similarity	NPC171888
0.9459	High Similarity	NPC469488
0.9459	High Similarity	NPC470777
0.9455	High Similarity	NPC176513
0.9455	High Similarity	NPC470775
0.945	High Similarity	NPC473798
0.9369	High Similarity	NPC297179
0.9364	High Similarity	NPC207217
0.9273	High Similarity	NPC143268
0.9273	High Similarity	NPC268238
0.9273	High Similarity	NPC45218
0.9273	High Similarity	NPC323821
0.9266	High Similarity	NPC474516
0.9266	High Similarity	NPC11252
0.9266	High Similarity	NPC289312
0.9252	High Similarity	NPC293850
0.9217	High Similarity	NPC24651
0.9211	High Similarity	NPC312833
0.9196	High Similarity	NPC470776
0.9189	High Similarity	NPC152199
0.9189	High Similarity	NPC16081
0.9189	High Similarity	NPC173686
0.9189	High Similarity	NPC235539
0.9189	High Similarity	NPC134869
0.9174	High Similarity	NPC201992
0.9159	High Similarity	NPC3316
0.9159	High Similarity	NPC144854
0.913	High Similarity	NPC105926
0.913	High Similarity	NPC265557
0.913	High Similarity	NPC91693
0.913	High Similarity	NPC18945
0.913	High Similarity	NPC67251
0.9099	High Similarity	NPC474906
0.9099	High Similarity	NPC18547
0.9074	High Similarity	NPC192813
0.9074	High Similarity	NPC277017
0.9074	High Similarity	NPC154608
0.9052	High Similarity	NPC476729
0.9018	High Similarity	NPC474734
0.9009	High Similarity	NPC51978
0.8957	High Similarity	NPC470779
0.8938	High Similarity	NPC473590
0.8919	High Similarity	NPC472002
0.8889	High Similarity	NPC102352
0.8889	High Similarity	NPC470922
0.885	High Similarity	NPC179626
0.8783	High Similarity	NPC476529
0.8783	High Similarity	NPC475775
0.8761	High Similarity	NPC117712
0.8761	High Similarity	NPC247069
0.8761	High Similarity	NPC243354
0.875	High Similarity	NPC302146
0.8739	High Similarity	NPC210005
0.8739	High Similarity	NPC470780
0.8739	High Similarity	NPC476008
0.8729	High Similarity	NPC473255
0.8718	High Similarity	NPC222688
0.8716	High Similarity	NPC181357
0.8707	High Similarity	NPC107338
0.8707	High Similarity	NPC109607
0.8684	High Similarity	NPC474046
0.8684	High Similarity	NPC470628
0.8684	High Similarity	NPC259306
0.8673	High Similarity	NPC198539
0.8673	High Similarity	NPC194273
0.8673	High Similarity	NPC477266
0.8673	High Similarity	NPC194100
0.8667	High Similarity	NPC188291
0.8661	High Similarity	NPC471243
0.8655	High Similarity	NPC225049
0.8655	High Similarity	NPC477745
0.8649	High Similarity	NPC141350
0.8624	High Similarity	NPC475036
0.8624	High Similarity	NPC65523
0.8609	High Similarity	NPC477116
0.8609	High Similarity	NPC146432
0.8609	High Similarity	NPC27999
0.8609	High Similarity	NPC309433
0.8609	High Similarity	NPC470778
0.8607	High Similarity	NPC100390
0.8607	High Similarity	NPC254614
0.8596	High Similarity	NPC470919
0.8596	High Similarity	NPC469877
0.8596	High Similarity	NPC299849
0.8584	High Similarity	NPC90769
0.8583	High Similarity	NPC470882
0.8571	High Similarity	NPC474567
0.8532	High Similarity	NPC275583
0.8522	High Similarity	NPC89929
0.8522	High Similarity	NPC213084
0.8522	High Similarity	NPC190185
0.8512	High Similarity	NPC295220
0.8512	High Similarity	NPC475636
0.8509	High Similarity	NPC94509
0.8509	High Similarity	NPC320118
0.85	High Similarity	NPC181999
0.85	High Similarity	NPC285091
0.85	High Similarity	NPC87662
0.8496	Intermediate Similarity	NPC157476
0.8487	Intermediate Similarity	NPC227397
0.8482	Intermediate Similarity	NPC310546
0.8482	Intermediate Similarity	NPC143706
0.8482	Intermediate Similarity	NPC472534
0.8482	Intermediate Similarity	NPC27814
0.8475	Intermediate Similarity	NPC470921
0.8468	Intermediate Similarity	NPC230541
0.8468	Intermediate Similarity	NPC202524
0.8462	Intermediate Similarity	NPC268958
0.8455	Intermediate Similarity	NPC102316
0.8455	Intermediate Similarity	NPC33378
0.8455	Intermediate Similarity	NPC6274
0.8455	Intermediate Similarity	NPC254146
0.8448	Intermediate Similarity	NPC98249
0.8448	Intermediate Similarity	NPC58662
0.8448	Intermediate Similarity	NPC469684
0.8448	Intermediate Similarity	NPC473968
0.8448	Intermediate Similarity	NPC53396
0.8443	Intermediate Similarity	NPC309096
0.8443	Intermediate Similarity	NPC264192
0.8443	Intermediate Similarity	NPC231529
0.8443	Intermediate Similarity	NPC54614
0.843	Intermediate Similarity	NPC473265
0.8426	Intermediate Similarity	NPC472972
0.8421	Intermediate Similarity	NPC280782
0.8421	Intermediate Similarity	NPC473397
0.8421	Intermediate Similarity	NPC193948
0.8421	Intermediate Similarity	NPC269530
0.8413	Intermediate Similarity	NPC596
0.8407	Intermediate Similarity	NPC85391
0.8407	Intermediate Similarity	NPC100908
0.8403	Intermediate Similarity	NPC471965
0.8403	Intermediate Similarity	NPC269642
0.84	Intermediate Similarity	NPC262813
0.8393	Intermediate Similarity	NPC94942
0.8393	Intermediate Similarity	NPC289702
0.8393	Intermediate Similarity	NPC208461
0.8393	Intermediate Similarity	NPC273155
0.839	Intermediate Similarity	NPC472004
0.839	Intermediate Similarity	NPC476961
0.839	Intermediate Similarity	NPC478051
0.8387	Intermediate Similarity	NPC168879
0.8376	Intermediate Similarity	NPC284707
0.8376	Intermediate Similarity	NPC106644
0.8348	Intermediate Similarity	NPC471252
0.8348	Intermediate Similarity	NPC477126
0.8347	Intermediate Similarity	NPC47113
0.8347	Intermediate Similarity	NPC293112
0.8347	Intermediate Similarity	NPC473635
0.8347	Intermediate Similarity	NPC174367
0.8333	Intermediate Similarity	NPC213320
0.8333	Intermediate Similarity	NPC469656
0.8333	Intermediate Similarity	NPC478066
0.8333	Intermediate Similarity	NPC11895
0.8333	Intermediate Similarity	NPC135038
0.8333	Intermediate Similarity	NPC243014
0.8333	Intermediate Similarity	NPC34315
0.8333	Intermediate Similarity	NPC14617
0.8333	Intermediate Similarity	NPC188738
0.8333	Intermediate Similarity	NPC43252
0.8333	Intermediate Similarity	NPC190065
0.8333	Intermediate Similarity	NPC471964
0.8333	Intermediate Similarity	NPC262199
0.8333	Intermediate Similarity	NPC29505
0.8333	Intermediate Similarity	NPC471961
0.8333	Intermediate Similarity	NPC141215
0.8333	Intermediate Similarity	NPC202666
0.8333	Intermediate Similarity	NPC251998
0.8333	Intermediate Similarity	NPC474229
0.8333	Intermediate Similarity	NPC469655
0.8333	Intermediate Similarity	NPC474846
0.8333	Intermediate Similarity	NPC472003
0.8333	Intermediate Similarity	NPC471089
0.8319	Intermediate Similarity	NPC472401
0.8319	Intermediate Similarity	NPC474242
0.8319	Intermediate Similarity	NPC75417
0.8319	Intermediate Similarity	NPC275675
0.8305	Intermediate Similarity	NPC473636
0.8305	Intermediate Similarity	NPC473203
0.8305	Intermediate Similarity	NPC319570
0.8305	Intermediate Similarity	NPC77689
0.8304	Intermediate Similarity	NPC166993

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 NPC470854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1727
0.2-0.3	3835
0.3-0.4	2123
0.4-0.5	683
0.5-0.6	298
0.6-0.7	133
0.7-0.8	123
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD6319	Approved
0.8333	Intermediate Similarity	NPD8328	Phase 3
0.8034	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.7983	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7492	Approved
0.7949	Intermediate Similarity	NPD8297	Approved
0.7934	Intermediate Similarity	NPD6054	Approved
0.7934	Intermediate Similarity	NPD6059	Approved
0.792	Intermediate Similarity	NPD7736	Approved
0.7903	Intermediate Similarity	NPD6616	Approved
0.7895	Intermediate Similarity	NPD6675	Approved
0.7895	Intermediate Similarity	NPD6402	Approved
0.7895	Intermediate Similarity	NPD5739	Approved
0.7895	Intermediate Similarity	NPD7128	Approved
0.7869	Intermediate Similarity	NPD6016	Approved
0.7869	Intermediate Similarity	NPD6015	Approved
0.7863	Intermediate Similarity	NPD6650	Approved
0.7863	Intermediate Similarity	NPD6649	Approved
0.7845	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7078	Approved
0.784	Intermediate Similarity	NPD8293	Discontinued
0.7826	Intermediate Similarity	NPD5701	Approved
0.7826	Intermediate Similarity	NPD5697	Approved
0.7805	Intermediate Similarity	NPD6370	Approved
0.7805	Intermediate Similarity	NPD5988	Approved
0.7778	Intermediate Similarity	NPD4634	Approved
0.7778	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6899	Approved
0.7759	Intermediate Similarity	NPD7320	Approved
0.7759	Intermediate Similarity	NPD6881	Approved
0.7739	Intermediate Similarity	NPD6008	Approved
0.7724	Intermediate Similarity	NPD6921	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD6013	Approved
0.7692	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6012	Approved
0.7686	Intermediate Similarity	NPD6009	Approved
0.7686	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD6882	Approved
0.7627	Intermediate Similarity	NPD7102	Approved
0.7627	Intermediate Similarity	NPD7290	Approved
0.7627	Intermediate Similarity	NPD6883	Approved
0.7607	Intermediate Similarity	NPD6011	Approved
0.7589	Intermediate Similarity	NPD4755	Approved
0.7581	Intermediate Similarity	NPD5983	Phase 2
0.7563	Intermediate Similarity	NPD6869	Approved
0.7563	Intermediate Similarity	NPD6847	Approved
0.7563	Intermediate Similarity	NPD8130	Phase 1
0.7563	Intermediate Similarity	NPD6617	Approved
0.7522	Intermediate Similarity	NPD4225	Approved
0.7521	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7507	Approved
0.746	Intermediate Similarity	NPD7604	Phase 2
0.7456	Intermediate Similarity	NPD5285	Approved
0.7456	Intermediate Similarity	NPD5286	Approved
0.7456	Intermediate Similarity	NPD4700	Approved
0.7456	Intermediate Similarity	NPD4696	Approved
0.7434	Intermediate Similarity	NPD7902	Approved
0.7417	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6033	Approved
0.7345	Intermediate Similarity	NPD4697	Phase 3
0.7344	Intermediate Similarity	NPD6336	Discontinued
0.7328	Intermediate Similarity	NPD5224	Approved
0.7328	Intermediate Similarity	NPD5211	Phase 2
0.7328	Intermediate Similarity	NPD5225	Approved
0.7328	Intermediate Similarity	NPD4633	Approved
0.7328	Intermediate Similarity	NPD5226	Approved
0.7321	Intermediate Similarity	NPD7748	Approved
0.7321	Intermediate Similarity	NPD5282	Discontinued
0.7317	Intermediate Similarity	NPD6274	Approved
0.7311	Intermediate Similarity	NPD6686	Approved
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7302	Intermediate Similarity	NPD8515	Approved
0.7302	Intermediate Similarity	NPD8516	Approved
0.7302	Intermediate Similarity	NPD8517	Approved
0.7297	Intermediate Similarity	NPD7515	Phase 2
0.7288	Intermediate Similarity	NPD4768	Approved
0.7288	Intermediate Similarity	NPD4767	Approved
0.7281	Intermediate Similarity	NPD6083	Phase 2
0.7281	Intermediate Similarity	NPD6084	Phase 2
0.728	Intermediate Similarity	NPD7516	Approved
0.7265	Intermediate Similarity	NPD5174	Approved
0.7265	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD3573	Approved
0.7241	Intermediate Similarity	NPD5223	Approved
0.7232	Intermediate Similarity	NPD6399	Phase 3
0.7217	Intermediate Similarity	NPD5696	Approved
0.7203	Intermediate Similarity	NPD5141	Approved
0.72	Intermediate Similarity	NPD7327	Approved
0.72	Intermediate Similarity	NPD7328	Approved
0.7193	Intermediate Similarity	NPD5221	Approved
0.7193	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5222	Approved
0.7168	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7900	Approved
0.7167	Intermediate Similarity	NPD4729	Approved
0.7167	Intermediate Similarity	NPD4730	Approved
0.7165	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD5173	Approved
0.712	Intermediate Similarity	NPD6317	Approved
0.7119	Intermediate Similarity	NPD4754	Approved
0.7117	Intermediate Similarity	NPD5328	Approved
0.7105	Intermediate Similarity	NPD5695	Phase 3
0.7069	Intermediate Similarity	NPD7638	Approved
0.7063	Intermediate Similarity	NPD6335	Approved
0.7063	Intermediate Similarity	NPD6314	Approved
0.7063	Intermediate Similarity	NPD6313	Approved
0.7049	Intermediate Similarity	NPD5247	Approved
0.7049	Intermediate Similarity	NPD5248	Approved
0.7049	Intermediate Similarity	NPD5249	Phase 3
0.7049	Intermediate Similarity	NPD5250	Approved
0.7049	Intermediate Similarity	NPD5251	Approved
0.7031	Intermediate Similarity	NPD6909	Approved
0.7031	Intermediate Similarity	NPD6908	Approved
0.7025	Intermediate Similarity	NPD5128	Approved
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.6991	Remote Similarity	NPD6079	Approved
0.6964	Remote Similarity	NPD4753	Phase 2
0.6964	Remote Similarity	NPD6101	Approved
0.6964	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD6868	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8033	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6894	Remote Similarity	NPD8074	Phase 3
0.688	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6855	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5215	Approved
0.6855	Remote Similarity	NPD5217	Approved
0.6855	Remote Similarity	NPD5216	Approved
0.6847	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8294	Approved
0.6822	Remote Similarity	NPD8377	Approved
0.6815	Remote Similarity	NPD7260	Phase 2
0.681	Remote Similarity	NPD5210	Approved
0.681	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4629	Approved
0.681	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1700	Approved
0.6807	Remote Similarity	NPD5344	Discontinued
0.6789	Remote Similarity	NPD3667	Approved
0.6783	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5778	Approved
0.6774	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5135	Approved
0.6774	Remote Similarity	NPD5169	Approved
0.6774	Remote Similarity	NPD6371	Approved
0.6769	Remote Similarity	NPD7503	Approved
0.6754	Remote Similarity	NPD46	Approved
0.6754	Remote Similarity	NPD6698	Approved
0.6741	Remote Similarity	NPD5956	Approved
0.6726	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5127	Approved
0.6696	Remote Similarity	NPD7334	Approved
0.6696	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD6684	Approved
0.6696	Remote Similarity	NPD7521	Approved
0.6696	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD6409	Approved
0.6696	Remote Similarity	NPD7146	Approved
0.6696	Remote Similarity	NPD5330	Approved
0.6696	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6643	Remote Similarity	NPD6333	Approved
0.6643	Remote Similarity	NPD6334	Approved
0.6642	Remote Similarity	NPD6845	Suspended
0.6615	Remote Similarity	NPD4522	Approved
0.6613	Remote Similarity	NPD5168	Approved
0.6606	Remote Similarity	NPD4695	Discontinued
0.6581	Remote Similarity	NPD6001	Approved
0.6579	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD5167	Approved
0.6552	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD5281	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