NPASS Compound

Structure

NPC269333 OpenBabel07101719252D 25 29 0 0 1 0 0 0 0 0999 V2000 -2.1636 -2.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 -1.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1183 -0.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9990 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4875 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4308 0.1846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9194 0.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7125 2.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2181 -2.1847 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4308 1.7487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9194 -1.2654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 1.9333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5115 0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5115 1.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8372 0.4833 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 -0.5712 -2.9031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 0.8831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 7 1 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 1 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 6 0 0 0 14 17 1 1 0 0 0 15 18 1 1 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 18 19 1 1 0 0 0 19 10 1 1 0 0 0 20 21 1 6 0 0 0 20 24 1 0 0 0 0 21 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.25
Volume:	364.151
LogP:	1.706
LogD:	1.244
LogS:	-3.568
# Rotatable Bonds:	1
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	5.514
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.187
MDCK Permeability:	6.33535091765225e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.168
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.765
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.37
Plasma Protein Binding (PPB):	83.94039916992188%
Volume Distribution (VD):	0.793
Pgp-substrate:	9.391762733459473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.356
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.417
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	2.677
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.788
Carcinogencity:	0.101
Eye Corrosion:	0.012
Eye Irritation:	0.168
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC269333

Natural Product ID:	NPC269333
*Common Name:**	YMAXHUPCQQAPPC-OKGXHQFUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YMAXHUPCQQAPPC-OKGXHQFUSA-N
Standard InCHI:	InChI=1S/C21H34O4/c1-12(22)14-5-9-21(25)17(14,2)8-6-15-18(3)7-4-13-10-19(13,18)16(23)11-20(15,21)24/h12-16,22-25H,4-11H2,1-3H3/t12-,13-,14-,15-,16-,17-,18-,19+,20+,21-/m1/s1
SMILES:	C[C@H]([C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@@]2(O)C[C@H]([C@]23[C@]1(C)CC[C@@H]3C2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558439
PubChem CID:	44179107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids

*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
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	138500.0	nM	PMID[470561]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	100600.0	nM	PMID[470561]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	165400.0	nM	PMID[470561]

☑ 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 NPC269333 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	442
0.1-0.2	4790
0.2-0.3	15522
0.3-0.4	9726
0.4-0.5	5649
0.5-0.6	4667
0.6-0.7	1494
0.7-0.8	347
0.8-0.85	47
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC287452
0.92	High Similarity	NPC477227
0.92	High Similarity	NPC192046
0.92	High Similarity	NPC105208
0.92	High Similarity	NPC128951
0.92	High Similarity	NPC302578
0.9079	High Similarity	NPC67657
0.9079	High Similarity	NPC147993
0.9079	High Similarity	NPC18857
0.9067	High Similarity	NPC163597
0.9012	High Similarity	NPC5943
0.8947	High Similarity	NPC185915
0.8933	High Similarity	NPC317242
0.8933	High Similarity	NPC243027
0.8933	High Similarity	NPC196136
0.8933	High Similarity	NPC158208
0.8889	High Similarity	NPC131365
0.8861	High Similarity	NPC475388
0.88	High Similarity	NPC10476
0.88	High Similarity	NPC228994
0.88	High Similarity	NPC192501
0.88	High Similarity	NPC304499
0.8684	High Similarity	NPC131584
0.8684	High Similarity	NPC139765
0.8667	High Similarity	NPC153719
0.8667	High Similarity	NPC470610
0.863	High Similarity	NPC474756
0.8553	High Similarity	NPC48795
0.8553	High Similarity	NPC475458
0.8519	High Similarity	NPC478054
0.8481	Intermediate Similarity	NPC81074
0.8481	Intermediate Similarity	NPC477282
0.84	Intermediate Similarity	NPC251201
0.84	Intermediate Similarity	NPC232925
0.84	Intermediate Similarity	NPC63588
0.8375	Intermediate Similarity	NPC66766
0.8375	Intermediate Similarity	NPC16449
0.8375	Intermediate Similarity	NPC117137
0.8313	Intermediate Similarity	NPC266651
0.8267	Intermediate Similarity	NPC477820
0.8267	Intermediate Similarity	NPC470833
0.8267	Intermediate Similarity	NPC470830
0.8267	Intermediate Similarity	NPC66407
0.8267	Intermediate Similarity	NPC241085
0.8267	Intermediate Similarity	NPC299948
0.8267	Intermediate Similarity	NPC107919
0.8228	Intermediate Similarity	NPC476233
0.8228	Intermediate Similarity	NPC133596
0.8228	Intermediate Similarity	NPC64081
0.8228	Intermediate Similarity	NPC474574
0.8228	Intermediate Similarity	NPC11907
0.8219	Intermediate Similarity	NPC472946
0.8214	Intermediate Similarity	NPC121981
0.8193	Intermediate Similarity	NPC320824
0.8171	Intermediate Similarity	NPC202688
0.8171	Intermediate Similarity	NPC60018
0.8171	Intermediate Similarity	NPC154043
0.8125	Intermediate Similarity	NPC471769
0.8118	Intermediate Similarity	NPC472396
0.8101	Intermediate Similarity	NPC470145
0.8072	Intermediate Similarity	NPC216420
0.8072	Intermediate Similarity	NPC69953
0.8072	Intermediate Similarity	NPC85095
0.8072	Intermediate Similarity	NPC211135
0.8052	Intermediate Similarity	NPC1340
0.8052	Intermediate Similarity	NPC187471
0.8052	Intermediate Similarity	NPC127094
0.8052	Intermediate Similarity	NPC470071
0.8052	Intermediate Similarity	NPC252182
0.8023	Intermediate Similarity	NPC128475
0.8	Intermediate Similarity	NPC63190
0.8	Intermediate Similarity	NPC145245
0.8	Intermediate Similarity	NPC475884
0.8	Intermediate Similarity	NPC473230
0.7976	Intermediate Similarity	NPC474156
0.7976	Intermediate Similarity	NPC255882
0.7975	Intermediate Similarity	NPC472952
0.7975	Intermediate Similarity	NPC270306
0.7975	Intermediate Similarity	NPC472950
0.7975	Intermediate Similarity	NPC91387
0.7975	Intermediate Similarity	NPC231680
0.7955	Intermediate Similarity	NPC473066
0.7949	Intermediate Similarity	NPC472341
0.7949	Intermediate Similarity	NPC473238
0.7945	Intermediate Similarity	NPC209686
0.7945	Intermediate Similarity	NPC249078
0.7945	Intermediate Similarity	NPC236099
0.7931	Intermediate Similarity	NPC228059
0.7931	Intermediate Similarity	NPC109744
0.7927	Intermediate Similarity	NPC474714
0.7922	Intermediate Similarity	NPC231945
0.7922	Intermediate Similarity	NPC192192
0.7907	Intermediate Similarity	NPC210658
0.7907	Intermediate Similarity	NPC161928
0.7882	Intermediate Similarity	NPC273290
0.7882	Intermediate Similarity	NPC232044
0.7875	Intermediate Similarity	NPC473916
0.7875	Intermediate Similarity	NPC477602
0.7875	Intermediate Similarity	NPC477601
0.7867	Intermediate Similarity	NPC44122
0.7857	Intermediate Similarity	NPC29342
0.7857	Intermediate Similarity	NPC2572
0.7857	Intermediate Similarity	NPC232023
0.7848	Intermediate Similarity	NPC470151
0.7841	Intermediate Similarity	NPC475751
0.7841	Intermediate Similarity	NPC473956
0.7838	Intermediate Similarity	NPC94897
0.7831	Intermediate Similarity	NPC473257
0.7831	Intermediate Similarity	NPC469745
0.7821	Intermediate Similarity	NPC131506
0.7821	Intermediate Similarity	NPC157777
0.7808	Intermediate Similarity	NPC185547
0.7808	Intermediate Similarity	NPC95804
0.7792	Intermediate Similarity	NPC254037
0.7792	Intermediate Similarity	NPC129829
0.7791	Intermediate Similarity	NPC155531
0.7791	Intermediate Similarity	NPC215968
0.7791	Intermediate Similarity	NPC471240
0.7778	Intermediate Similarity	NPC3538
0.7778	Intermediate Similarity	NPC477224
0.7778	Intermediate Similarity	NPC113500
0.7778	Intermediate Similarity	NPC175
0.7778	Intermediate Similarity	NPC30687
0.7765	Intermediate Similarity	NPC242016
0.7765	Intermediate Similarity	NPC227260
0.7753	Intermediate Similarity	NPC293609
0.7738	Intermediate Similarity	NPC470611
0.7733	Intermediate Similarity	NPC41577
0.7733	Intermediate Similarity	NPC243469
0.7733	Intermediate Similarity	NPC474380
0.7733	Intermediate Similarity	NPC475943
0.7733	Intermediate Similarity	NPC190827
0.7733	Intermediate Similarity	NPC473276
0.7727	Intermediate Similarity	NPC20822
0.7701	Intermediate Similarity	NPC263802
0.7701	Intermediate Similarity	NPC186145
0.7701	Intermediate Similarity	NPC474657
0.7701	Intermediate Similarity	NPC202937
0.7692	Intermediate Similarity	NPC473067
0.7692	Intermediate Similarity	NPC473064
0.7692	Intermediate Similarity	NPC473065
0.7683	Intermediate Similarity	NPC471045
0.7667	Intermediate Similarity	NPC277774
0.7667	Intermediate Similarity	NPC211845
0.7667	Intermediate Similarity	NPC167644
0.7667	Intermediate Similarity	NPC256104
0.7667	Intermediate Similarity	NPC182740
0.7667	Intermediate Similarity	NPC311246
0.7667	Intermediate Similarity	NPC122083
0.7662	Intermediate Similarity	NPC472741
0.7647	Intermediate Similarity	NPC477285
0.7647	Intermediate Similarity	NPC470070
0.7647	Intermediate Similarity	NPC111582
0.764	Intermediate Similarity	NPC279329
0.7625	Intermediate Similarity	NPC478130
0.7614	Intermediate Similarity	NPC475664
0.7614	Intermediate Similarity	NPC475817
0.7614	Intermediate Similarity	NPC473436
0.7609	Intermediate Similarity	NPC476510
0.7609	Intermediate Similarity	NPC142264
0.7609	Intermediate Similarity	NPC156377
0.76	Intermediate Similarity	NPC118937
0.76	Intermediate Similarity	NPC159654
0.76	Intermediate Similarity	NPC69149
0.76	Intermediate Similarity	NPC281540
0.76	Intermediate Similarity	NPC167995
0.7595	Intermediate Similarity	NPC100586
0.7595	Intermediate Similarity	NPC195530
0.7595	Intermediate Similarity	NPC8004
0.7595	Intermediate Similarity	NPC473279
0.7595	Intermediate Similarity	NPC127283
0.7595	Intermediate Similarity	NPC157422
0.7595	Intermediate Similarity	NPC109457
0.759	Intermediate Similarity	NPC476176
0.759	Intermediate Similarity	NPC329871
0.7586	Intermediate Similarity	NPC472272
0.7586	Intermediate Similarity	NPC6605
0.7586	Intermediate Similarity	NPC477283
0.7586	Intermediate Similarity	NPC269058
0.7586	Intermediate Similarity	NPC474448
0.7586	Intermediate Similarity	NPC71520
0.7586	Intermediate Similarity	NPC476727
0.7586	Intermediate Similarity	NPC64862
0.7586	Intermediate Similarity	NPC476726
0.7586	Intermediate Similarity	NPC201273
0.7564	Intermediate Similarity	NPC99264
0.7556	Intermediate Similarity	NPC59006
0.7556	Intermediate Similarity	NPC36372
0.7556	Intermediate Similarity	NPC5632
0.7556	Intermediate Similarity	NPC275671
0.7556	Intermediate Similarity	NPC149966
0.7534	Intermediate Similarity	NPC95958
0.7532	Intermediate Similarity	NPC48079
0.7531	Intermediate Similarity	NPC186851
0.7529	Intermediate Similarity	NPC286719
0.7529	Intermediate Similarity	NPC477286
0.7529	Intermediate Similarity	NPC296734
0.7529	Intermediate Similarity	NPC477446
0.7529	Intermediate Similarity	NPC121121
0.7529	Intermediate Similarity	NPC470155

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 NPC269333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	4703
0.2-0.3	2843
0.3-0.4	655
0.4-0.5	236
0.5-0.6	227
0.6-0.7	42
0.7-0.8	3
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
0.8267	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4787	Phase 1
0.7294	Intermediate Similarity	NPD6928	Phase 2
0.7143	Intermediate Similarity	NPD371	Approved
0.7097	Intermediate Similarity	NPD8171	Discontinued
0.7059	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD6697	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.6941	Remote Similarity	NPD6116	Phase 1
0.6897	Remote Similarity	NPD7525	Registered
0.6824	Remote Similarity	NPD6117	Approved
0.6747	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3703	Phase 2
0.6627	Remote Similarity	NPD4244	Approved
0.6627	Remote Similarity	NPD4245	Approved
0.6588	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7524	Approved
0.6506	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3698	Phase 2
0.6506	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1700	Approved
0.642	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5360	Phase 3
0.6333	Remote Similarity	NPD6931	Approved
0.6333	Remote Similarity	NPD4748	Discontinued
0.6333	Remote Similarity	NPD6930	Phase 2
0.6304	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD4159	Approved
0.6263	Remote Similarity	NPD7991	Discontinued
0.625	Remote Similarity	NPD6933	Approved
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7516	Approved
0.6235	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4789	Approved
0.6222	Remote Similarity	NPD6929	Approved
0.6211	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6705	Phase 1
0.6186	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6700	Approved
0.618	Remote Similarity	NPD6932	Approved
0.6161	Remote Similarity	NPD7328	Approved
0.6161	Remote Similarity	NPD7327	Approved
0.6139	Remote Similarity	NPD4755	Approved
0.6136	Remote Similarity	NPD6942	Approved
0.6136	Remote Similarity	NPD3702	Approved
0.6136	Remote Similarity	NPD7339	Approved
0.6122	Remote Similarity	NPD6702	Approved
0.6122	Remote Similarity	NPD6703	Approved
0.6111	Remote Similarity	NPD4634	Approved
0.6087	Remote Similarity	NPD6902	Approved
0.6075	Remote Similarity	NPD7320	Approved
0.6061	Remote Similarity	NPD4202	Approved
0.6044	Remote Similarity	NPD6683	Phase 2
0.6042	Remote Similarity	NPD7750	Discontinued
0.6023	Remote Similarity	NPD6924	Approved
0.6023	Remote Similarity	NPD6926	Approved
0.6019	Remote Similarity	NPD4700	Approved
0.6019	Remote Similarity	NPD5285	Approved
0.6019	Remote Similarity	NPD4696	Approved
0.6019	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8380	Approved
0.5978	Remote Similarity	NPD7514	Phase 3
0.5977	Remote Similarity	NPD4243	Approved
0.5977	Remote Similarity	NPD4758	Discontinued
0.5957	Remote Similarity	NPD4788	Approved
0.5934	Remote Similarity	NPD7145	Approved
0.5934	Remote Similarity	NPD5364	Discontinued
0.5934	Remote Similarity	NPD3671	Phase 1
0.5913	Remote Similarity	NPD8377	Approved
0.5913	Remote Similarity	NPD8294	Approved
0.5905	Remote Similarity	NPD5211	Phase 2
0.5905	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD5224	Approved
0.5905	Remote Similarity	NPD5225	Approved
0.5905	Remote Similarity	NPD5226	Approved
0.589	Remote Similarity	NPD385	Approved
0.589	Remote Similarity	NPD384	Approved
0.5888	Remote Similarity	NPD7128	Approved
0.5888	Remote Similarity	NPD6675	Approved
0.5888	Remote Similarity	NPD5739	Approved
0.5888	Remote Similarity	NPD6402	Approved
0.5872	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7645	Phase 2
0.5862	Remote Similarity	NPD8033	Approved
0.5849	Remote Similarity	NPD5174	Approved
0.5849	Remote Similarity	NPD5175	Approved
0.5843	Remote Similarity	NPD4784	Approved
0.5843	Remote Similarity	NPD1810	Approved
0.5843	Remote Similarity	NPD4785	Approved
0.5843	Remote Similarity	NPD1811	Approved
0.581	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD7332	Phase 2
0.5806	Remote Similarity	NPD7509	Discontinued
0.5804	Remote Similarity	NPD4632	Approved
0.58	Remote Similarity	NPD8034	Phase 2
0.58	Remote Similarity	NPD8035	Phase 2
0.58	Remote Similarity	NPD7087	Discontinued
0.5795	Remote Similarity	NPD5777	Approved
0.5795	Remote Similarity	NPD6081	Approved
0.5794	Remote Similarity	NPD5141	Approved
0.578	Remote Similarity	NPD6899	Approved
0.578	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6881	Approved
0.5776	Remote Similarity	NPD6054	Approved
0.5776	Remote Similarity	NPD6059	Approved
0.5769	Remote Similarity	NPD7638	Approved
0.5758	Remote Similarity	NPD5328	Approved
0.5758	Remote Similarity	NPD4753	Phase 2
0.5753	Remote Similarity	NPD386	Approved
0.5753	Remote Similarity	NPD388	Approved
0.5745	Remote Similarity	NPD6898	Phase 1
0.5741	Remote Similarity	NPD4767	Approved
0.5741	Remote Similarity	NPD4768	Approved
0.5729	Remote Similarity	NPD4786	Approved
0.5727	Remote Similarity	NPD6372	Approved
0.5727	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD8418	Phase 2
0.5714	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5701	Remote Similarity	NPD4754	Approved
0.5688	Remote Similarity	NPD5697	Approved
0.5688	Remote Similarity	NPD5701	Approved
0.5688	Remote Similarity	NPD6412	Phase 2
0.5678	Remote Similarity	NPD6370	Approved
0.5676	Remote Similarity	NPD6883	Approved
0.5676	Remote Similarity	NPD7102	Approved
0.5676	Remote Similarity	NPD7290	Approved
0.5667	Remote Similarity	NPD7507	Approved
0.5664	Remote Similarity	NPD8133	Approved
0.5656	Remote Similarity	NPD7319	Approved
0.5644	Remote Similarity	NPD6079	Approved
0.5641	Remote Similarity	NPD6319	Approved
0.5636	Remote Similarity	NPD4729	Approved
0.5636	Remote Similarity	NPD5128	Approved
0.5636	Remote Similarity	NPD4730	Approved
0.563	Remote Similarity	NPD7604	Phase 2
0.5625	Remote Similarity	NPD6869	Approved
0.5625	Remote Similarity	NPD8130	Phase 1
0.5625	Remote Similarity	NPD586	Phase 1
0.5625	Remote Similarity	NPD6650	Approved
0.5625	Remote Similarity	NPD6617	Approved
0.5625	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD6847	Approved
0.562	Remote Similarity	NPD7078	Approved
0.5618	Remote Similarity	NPD7151	Approved
0.5618	Remote Similarity	NPD7150	Approved
0.5618	Remote Similarity	NPD7152	Approved
0.5612	Remote Similarity	NPD8308	Discontinued
0.5612	Remote Similarity	NPD3618	Phase 1
0.5607	Remote Similarity	NPD7632	Discontinued
0.5604	Remote Similarity	NPD4190	Phase 3
0.5604	Remote Similarity	NPD5275	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