NPASS Compound

Structure

NPC92139 OpenBabel07101718202D 31 35 0 0 1 0 0 0 0 0999 V2000 6.9064 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4203 -2.0357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4083 -3.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5332 -0.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4083 0.5251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0598 -1.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7244 -2.3915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5663 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3973 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 -1.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 -4.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2503 -3.8499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3642 0.0178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2503 -0.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8568 -1.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7244 -1.4193 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0019 -0.7688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4686 -0.5637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0922 -2.3915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4083 -2.3915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9342 -3.8499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9391 0.2516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9342 -2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2503 -2.8776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5663 -0.9332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4083 -1.4193 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0509 -0.9709 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4395 -0.6146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7762 -4.3360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2875 1.1593 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 23 1 0 0 0 0 2 23 1 0 0 0 0 4 25 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 9 1 1 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 6 0 0 0 19 23 1 0 0 0 0 19 24 1 1 0 0 0 20 24 1 1 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 29 2 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 24 3 1 1 0 0 0 25 26 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	462.654
LogP:	3.999
LogD:	4.257
LogS:	-4.421
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	4.886
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.166
MDCK Permeability:	5.1255519792903215e-05
Pgp-inhibitor:	0.882
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	90.1825180053711%
Volume Distribution (VD):	1.1
Pgp-substrate:	3.2840654850006104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.472
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.814
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	3.916
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.464
Carcinogencity:	0.035
Eye Corrosion:	0.181
Eye Irritation:	0.552
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC92139

Natural Product ID:	NPC92139
*Common Name:**	23Alpha-Hydroxy-3-Oxo-25,26,27-Trinordammar-24,20-Alpha-Olide
IUPAC Name:	(3S,5S)-3-hydroxy-5-methyl-5-[(5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-one
Synonyms:
Standard InCHIKey:	MPOXZUFJPWKCSZ-VWADOUGUSA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-23(2)19-10-14-26(5)20(24(19,3)12-11-21(23)29)8-7-16-17(9-13-25(16,26)4)27(6)15-18(28)22(30)31-27/h16-20,28H,7-15H2,1-6H3/t16-,17+,18+,19+,20-,24+,25-,26-,27+/m1/s1
SMILES:	O=C1O[C@](C[C@@H]1O)(C)[C@H]1CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109469
PubChem CID:	76328407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8000.0	nM	PMID[453919]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26700.0	nM	PMID[453919]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	12400.0	nM	PMID[453919]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[453919]

☑ 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 NPC92139 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	370
0.1-0.2	3011
0.2-0.3	11122
0.3-0.4	11979
0.4-0.5	5902
0.5-0.6	6079
0.6-0.7	3518
0.7-0.8	639
0.8-0.85	60
0.85-0.9	15
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC206878
0.8795	High Similarity	NPC164289
0.8795	High Similarity	NPC242771
0.8795	High Similarity	NPC311642
0.8795	High Similarity	NPC100366
0.878	High Similarity	NPC472853
0.869	High Similarity	NPC268578
0.869	High Similarity	NPC259173
0.869	High Similarity	NPC292458
0.869	High Similarity	NPC217559
0.8675	High Similarity	NPC58631
0.8659	High Similarity	NPC31302
0.8659	High Similarity	NPC245029
0.8605	High Similarity	NPC474448
0.8571	High Similarity	NPC477935
0.8571	High Similarity	NPC102156
0.8571	High Similarity	NPC477936
0.8571	High Similarity	NPC148740
0.8537	High Similarity	NPC476732
0.8537	High Similarity	NPC199965
0.8471	Intermediate Similarity	NPC472744
0.8415	Intermediate Similarity	NPC180199
0.8415	Intermediate Similarity	NPC477919
0.8415	Intermediate Similarity	NPC264602
0.8415	Intermediate Similarity	NPC477918
0.8391	Intermediate Similarity	NPC80700
0.837	Intermediate Similarity	NPC116683
0.8293	Intermediate Similarity	NPC477933
0.8293	Intermediate Similarity	NPC477932
0.8272	Intermediate Similarity	NPC472945
0.8272	Intermediate Similarity	NPC472944
0.8261	Intermediate Similarity	NPC470031
0.825	Intermediate Similarity	NPC469940
0.825	Intermediate Similarity	NPC197701
0.8242	Intermediate Similarity	NPC228700
0.8235	Intermediate Similarity	NPC12933
0.8182	Intermediate Similarity	NPC472745
0.8171	Intermediate Similarity	NPC477934
0.8161	Intermediate Similarity	NPC474996
0.8152	Intermediate Similarity	NPC309127
0.8152	Intermediate Similarity	NPC470423
0.8152	Intermediate Similarity	NPC247877
0.814	Intermediate Similarity	NPC61107
0.814	Intermediate Similarity	NPC289486
0.814	Intermediate Similarity	NPC13494
0.814	Intermediate Similarity	NPC328007
0.814	Intermediate Similarity	NPC317066
0.8125	Intermediate Similarity	NPC477929
0.8095	Intermediate Similarity	NPC185465
0.8085	Intermediate Similarity	NPC470632
0.8072	Intermediate Similarity	NPC4209
0.8068	Intermediate Similarity	NPC477445
0.8049	Intermediate Similarity	NPC167702
0.8049	Intermediate Similarity	NPC472854
0.8049	Intermediate Similarity	NPC254340
0.8049	Intermediate Similarity	NPC477930
0.8049	Intermediate Similarity	NPC280026
0.8046	Intermediate Similarity	NPC477285
0.8046	Intermediate Similarity	NPC111582
0.8043	Intermediate Similarity	NPC472148
0.8043	Intermediate Similarity	NPC472147
0.8023	Intermediate Similarity	NPC190940
0.8023	Intermediate Similarity	NPC77311
0.8	Intermediate Similarity	NPC80891
0.8	Intermediate Similarity	NPC476734
0.8	Intermediate Similarity	NPC320144
0.8	Intermediate Similarity	NPC252032
0.8	Intermediate Similarity	NPC229407
0.8	Intermediate Similarity	NPC255176
0.8	Intermediate Similarity	NPC254572
0.8	Intermediate Similarity	NPC469941
0.8	Intermediate Similarity	NPC33398
0.8	Intermediate Similarity	NPC250687
0.8	Intermediate Similarity	NPC201276
0.8	Intermediate Similarity	NPC48824
0.8	Intermediate Similarity	NPC319671
0.798	Intermediate Similarity	NPC131665
0.798	Intermediate Similarity	NPC255387
0.7979	Intermediate Similarity	NPC476728
0.7978	Intermediate Similarity	NPC155531
0.7978	Intermediate Similarity	NPC114378
0.7978	Intermediate Similarity	NPC215968
0.7978	Intermediate Similarity	NPC103782
0.7976	Intermediate Similarity	NPC171658
0.7976	Intermediate Similarity	NPC474404
0.7976	Intermediate Similarity	NPC317913
0.7976	Intermediate Similarity	NPC207010
0.7957	Intermediate Similarity	NPC470424
0.7955	Intermediate Similarity	NPC473336
0.7955	Intermediate Similarity	NPC319909
0.7955	Intermediate Similarity	NPC471044
0.7955	Intermediate Similarity	NPC79308
0.7952	Intermediate Similarity	NPC212733
0.7952	Intermediate Similarity	NPC472311
0.7952	Intermediate Similarity	NPC179858
0.7935	Intermediate Similarity	NPC471747
0.7931	Intermediate Similarity	NPC121121
0.7931	Intermediate Similarity	NPC477286
0.7931	Intermediate Similarity	NPC286719
0.7912	Intermediate Similarity	NPC61688
0.7912	Intermediate Similarity	NPC269267
0.7907	Intermediate Similarity	NPC261616
0.7907	Intermediate Similarity	NPC470609
0.7895	Intermediate Similarity	NPC74466
0.7889	Intermediate Similarity	NPC202937
0.7889	Intermediate Similarity	NPC251808
0.7889	Intermediate Similarity	NPC474174
0.7882	Intermediate Similarity	NPC34046
0.7882	Intermediate Similarity	NPC224802
0.7882	Intermediate Similarity	NPC80089
0.7882	Intermediate Similarity	NPC324700
0.7882	Intermediate Similarity	NPC171426
0.7872	Intermediate Similarity	NPC62407
0.7872	Intermediate Similarity	NPC287354
0.7872	Intermediate Similarity	NPC215570
0.7857	Intermediate Similarity	NPC471046
0.7849	Intermediate Similarity	NPC472231
0.7849	Intermediate Similarity	NPC472232
0.7841	Intermediate Similarity	NPC327451
0.7831	Intermediate Similarity	NPC317212
0.7826	Intermediate Similarity	NPC185529
0.7826	Intermediate Similarity	NPC472146
0.7826	Intermediate Similarity	NPC470114
0.7816	Intermediate Similarity	NPC280781
0.7816	Intermediate Similarity	NPC48756
0.7805	Intermediate Similarity	NPC58057
0.7805	Intermediate Similarity	NPC156277
0.7805	Intermediate Similarity	NPC151018
0.7805	Intermediate Similarity	NPC320549
0.7802	Intermediate Similarity	NPC201607
0.7802	Intermediate Similarity	NPC476435
0.7802	Intermediate Similarity	NPC471221
0.7802	Intermediate Similarity	NPC56777
0.7791	Intermediate Similarity	NPC472310
0.7778	Intermediate Similarity	NPC472272
0.7778	Intermediate Similarity	NPC476727
0.7778	Intermediate Similarity	NPC100078
0.7778	Intermediate Similarity	NPC477283
0.7778	Intermediate Similarity	NPC476726
0.7765	Intermediate Similarity	NPC23884
0.7765	Intermediate Similarity	NPC298168
0.7765	Intermediate Similarity	NPC143133
0.7765	Intermediate Similarity	NPC11907
0.7765	Intermediate Similarity	NPC307865
0.7765	Intermediate Similarity	NPC133596
0.7755	Intermediate Similarity	NPC213528
0.7755	Intermediate Similarity	NPC244969
0.7753	Intermediate Similarity	NPC473299
0.7753	Intermediate Similarity	NPC105895
0.7738	Intermediate Similarity	NPC27349
0.7738	Intermediate Similarity	NPC125767
0.7738	Intermediate Similarity	NPC21220
0.7738	Intermediate Similarity	NPC24014
0.7727	Intermediate Similarity	NPC60018
0.7727	Intermediate Similarity	NPC202688
0.7727	Intermediate Similarity	NPC30583
0.7727	Intermediate Similarity	NPC154043
0.7717	Intermediate Similarity	NPC24705
0.7717	Intermediate Similarity	NPC56962
0.7717	Intermediate Similarity	NPC200580
0.7711	Intermediate Similarity	NPC310766
0.7711	Intermediate Similarity	NPC232112
0.77	Intermediate Similarity	NPC166079
0.7692	Intermediate Similarity	NPC97002
0.7692	Intermediate Similarity	NPC470920
0.7692	Intermediate Similarity	NPC239938
0.7684	Intermediate Similarity	NPC30677
0.7684	Intermediate Similarity	NPC180557
0.7684	Intermediate Similarity	NPC469329
0.7684	Intermediate Similarity	NPC473415
0.7684	Intermediate Similarity	NPC37787
0.7683	Intermediate Similarity	NPC477850
0.7683	Intermediate Similarity	NPC108131
0.7674	Intermediate Similarity	NPC26029
0.7674	Intermediate Similarity	NPC329117
0.7667	Intermediate Similarity	NPC62572
0.766	Intermediate Similarity	NPC472237
0.766	Intermediate Similarity	NPC476189
0.766	Intermediate Similarity	NPC472238
0.7653	Intermediate Similarity	NPC178853
0.7653	Intermediate Similarity	NPC477052
0.7653	Intermediate Similarity	NPC477053
0.7653	Intermediate Similarity	NPC477051
0.7647	Intermediate Similarity	NPC472486
0.7647	Intermediate Similarity	NPC472487
0.7629	Intermediate Similarity	NPC253995
0.7625	Intermediate Similarity	NPC42060
0.7625	Intermediate Similarity	NPC268736
0.7625	Intermediate Similarity	NPC477931
0.7624	Intermediate Similarity	NPC203974
0.7614	Intermediate Similarity	NPC472230
0.7614	Intermediate Similarity	NPC232625
0.7614	Intermediate Similarity	NPC472229
0.7609	Intermediate Similarity	NPC476379
0.7604	Intermediate Similarity	NPC163685
0.7604	Intermediate Similarity	NPC475785
0.76	Intermediate Similarity	NPC471293
0.76	Intermediate Similarity	NPC327093
0.759	Intermediate Similarity	NPC89310
0.7586	Intermediate Similarity	NPC81074

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 NPC92139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	3284
0.2-0.3	3648
0.3-0.4	1083
0.4-0.5	318
0.5-0.6	238
0.6-0.7	148
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD4789	Approved
0.8072	Intermediate Similarity	NPD6117	Approved
0.8049	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6116	Phase 1
0.7882	Intermediate Similarity	NPD6114	Approved
0.7882	Intermediate Similarity	NPD6118	Approved
0.7882	Intermediate Similarity	NPD6115	Approved
0.7882	Intermediate Similarity	NPD6697	Approved
0.7805	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6081	Approved
0.7805	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5777	Approved
0.7738	Intermediate Similarity	NPD3702	Approved
0.7683	Intermediate Similarity	NPD4244	Approved
0.7683	Intermediate Similarity	NPD4245	Approved
0.7625	Intermediate Similarity	NPD4224	Phase 2
0.7561	Intermediate Similarity	NPD3698	Phase 2
0.7561	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5360	Phase 3
0.7439	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.7255	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8035	Phase 2
0.7188	Intermediate Similarity	NPD8034	Phase 2
0.7126	Intermediate Similarity	NPD3703	Phase 2
0.7113	Intermediate Similarity	NPD6399	Phase 3
0.71	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7320	Approved
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6977	Remote Similarity	NPD4758	Discontinued
0.697	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD1700	Approved
0.6944	Remote Similarity	NPD8297	Approved
0.6889	Remote Similarity	NPD3671	Phase 1
0.6889	Remote Similarity	NPD5364	Discontinued
0.6887	Remote Similarity	NPD6899	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6881	Approved
0.6882	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6650	Approved
0.6804	Remote Similarity	NPD4753	Phase 2
0.6792	Remote Similarity	NPD5697	Approved
0.6792	Remote Similarity	NPD5701	Approved
0.6759	Remote Similarity	NPD7290	Approved
0.6759	Remote Similarity	NPD6883	Approved
0.6759	Remote Similarity	NPD7102	Approved
0.6697	Remote Similarity	NPD6847	Approved
0.6697	Remote Similarity	NPD6617	Approved
0.6697	Remote Similarity	NPD6869	Approved
0.6697	Remote Similarity	NPD8130	Phase 1
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD6904	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.66	Remote Similarity	NPD8171	Discontinued
0.6581	Remote Similarity	NPD7492	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6559	Remote Similarity	NPD6928	Phase 2
0.6555	Remote Similarity	NPD7736	Approved
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6903	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6616	Approved
0.6522	Remote Similarity	NPD6054	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD6059	Approved
0.6505	Remote Similarity	NPD4755	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6477	Remote Similarity	NPD4787	Phase 1
0.6471	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD7078	Approved
0.6463	Remote Similarity	NPD3198	Approved
0.646	Remote Similarity	NPD6940	Discontinued
0.6449	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3667	Approved
0.641	Remote Similarity	NPD6370	Approved
0.6408	Remote Similarity	NPD4697	Phase 3
0.6392	Remote Similarity	NPD5329	Approved
0.6381	Remote Similarity	NPD5286	Approved
0.6381	Remote Similarity	NPD8418	Phase 2
0.6381	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD4700	Approved
0.6381	Remote Similarity	NPD4696	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7902	Approved
0.6344	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD3617	Approved
0.6344	Remote Similarity	NPD4238	Approved
0.6337	Remote Similarity	NPD5693	Phase 1
0.6337	Remote Similarity	NPD7515	Phase 2
0.6337	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD3618	Phase 1
0.6327	Remote Similarity	NPD5279	Phase 3
0.6325	Remote Similarity	NPD6016	Approved
0.6325	Remote Similarity	NPD6015	Approved
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6274	Approved
0.63	Remote Similarity	NPD5328	Approved
0.6293	Remote Similarity	NPD7100	Approved
0.6293	Remote Similarity	NPD7101	Approved
0.6289	Remote Similarity	NPD4197	Approved
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3665	Phase 1
0.6289	Remote Similarity	NPD3666	Approved
0.6286	Remote Similarity	NPD7638	Approved
0.6271	Remote Similarity	NPD5988	Approved
0.6262	Remote Similarity	NPD5225	Approved
0.6262	Remote Similarity	NPD4633	Approved
0.6262	Remote Similarity	NPD5224	Approved
0.6262	Remote Similarity	NPD5226	Approved
0.6262	Remote Similarity	NPD5211	Phase 2
0.6261	Remote Similarity	NPD6009	Approved
0.6261	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3730	Approved
0.625	Remote Similarity	NPD3728	Approved
0.625	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD6920	Discontinued
0.6239	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD5692	Phase 3
0.6238	Remote Similarity	NPD5207	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6218	Remote Similarity	NPD7604	Phase 2
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6001	Approved
0.6207	Remote Similarity	NPD6335	Approved
0.6204	Remote Similarity	NPD5174	Approved
0.6204	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD5173	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD6908	Approved
0.6186	Remote Similarity	NPD6909	Approved
0.6176	Remote Similarity	NPD5284	Approved
0.6176	Remote Similarity	NPD5281	Approved
0.6176	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD5694	Approved
0.6174	Remote Similarity	NPD6868	Approved
0.6168	Remote Similarity	NPD5223	Approved
0.6163	Remote Similarity	NPD7909	Approved
0.6161	Remote Similarity	NPD4634	Approved
0.6147	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4225	Approved
0.6126	Remote Similarity	NPD6686	Approved
0.6121	Remote Similarity	NPD6317	Approved
0.6117	Remote Similarity	NPD4202	Approved
0.6116	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD7632	Discontinued
0.6098	Remote Similarity	NPD7319	Approved
0.6091	Remote Similarity	NPD4767	Approved
0.6091	Remote Similarity	NPD4768	Approved
0.6083	Remote Similarity	NPD8328	Phase 3
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4221	Approved
0.6068	Remote Similarity	NPD6314	Approved
0.6068	Remote Similarity	NPD6313	Approved
0.6067	Remote Similarity	NPD229	Approved
0.6058	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6052	Approved
0.6055	Remote Similarity	NPD4754	Approved
0.6049	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7525	Registered

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