NPASS Compound

Structure

NPC268213 OpenBabel07101718322D 29 35 0 0 1 0 0 0 0 0999 V2000 0.1195 3.0811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1359 1.9232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8034 1.1367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9614 0.6505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8034 4.0533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7225 2.5950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6885 0.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9614 3.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5645 2.1089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2180 0.9413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6454 2.5950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8915 -0.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8034 2.1089 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6454 3.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1195 2.1089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1195 1.1367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2870 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9246 -0.3004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1299 -0.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6303 0.0241 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9614 2.5950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5645 1.1367 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1889 0.8904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7225 0.6505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4873 4.0533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6004 -1.5557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1008 -0.7912 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 -5.1598 0.8395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 1 0 0 0 14 25 2 0 0 0 0 15 16 1 0 0 0 0 15 21 1 6 0 0 0 16 24 1 1 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 18 24 1 1 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 1 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 1 1 6 0 0 0 22 24 1 6 0 0 0 23 10 1 6 0 0 0 23 29 1 0 0 0 0 24 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.21
Volume:	399.807
LogP:	3.593
LogD:	3.153
LogS:	-4.958
# Rotatable Bonds:	1
TPSA:	68.43
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	5.707
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	2.1659599951817654e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.117
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	83.28457641601562%
Volume Distribution (VD):	1.669
Pgp-substrate:	6.751938343048096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.237
CYP2C19-substrate:	0.572
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.462

ADMET: Excretion

Clearance (CL):	13.075
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.691
Human Hepatotoxicity (H-HT):	0.928
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.835
Carcinogencity:	0.891
Eye Corrosion:	0.091
Eye Irritation:	0.133
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC268213

Natural Product ID:	NPC268213
*Common Name:**	AMHVZECVAABXSC-BHZKGVBYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AMHVZECVAABXSC-BHZKGVBYSA-N
Standard InCHI:	InChI=1S/C24H30O5/c1-21-8-5-14(25)11-13(21)3-4-16-15(21)6-9-22(2)17(12-18-24(16,22)28-18)23-10-7-19(26)27-20(23)29-23/h7,10,13,15-18,20H,3-6,8-9,11-12H2,1-2H3/t13-,15+,16-,17+,18-,20-,21+,22-,23+,24-/m1/s1
SMILES:	C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](C[C@@H]3[C@]12O3)[C@@]12C=CC(=O)O[C@@H]1O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486200
PubChem CID:	25082522
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides and derivatives

*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
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]

☑ 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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	18.51	ug.mL-1	PMID[494242]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	8.54	ug.mL-1	PMID[494242]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	1300.0	nM	PMID[494243]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	4300.0	nM	PMID[494243]

☑ 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 NPC268213 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	308
0.1-0.2	1933
0.2-0.3	5772
0.3-0.4	11767
0.4-0.5	9594
0.5-0.6	7295
0.6-0.7	5081
0.7-0.8	923
0.8-0.85	19
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9174	High Similarity	NPC150228
0.9174	High Similarity	NPC214005
0.8929	High Similarity	NPC232564
0.8929	High Similarity	NPC113425
0.8378	Intermediate Similarity	NPC471601
0.8235	Intermediate Similarity	NPC204731
0.8211	Intermediate Similarity	NPC473593
0.8182	Intermediate Similarity	NPC8374
0.8174	Intermediate Similarity	NPC222834
0.8142	Intermediate Similarity	NPC61411
0.812	Intermediate Similarity	NPC190286
0.808	Intermediate Similarity	NPC231240
0.8067	Intermediate Similarity	NPC475834
0.8067	Intermediate Similarity	NPC474179
0.8065	Intermediate Similarity	NPC471407
0.8049	Intermediate Similarity	NPC287423
0.8033	Intermediate Similarity	NPC241456
0.8033	Intermediate Similarity	NPC32868
0.8017	Intermediate Similarity	NPC153700
0.8017	Intermediate Similarity	NPC115349
0.8017	Intermediate Similarity	NPC88326
0.8016	Intermediate Similarity	NPC316915
0.7984	Intermediate Similarity	NPC473620
0.7983	Intermediate Similarity	NPC153440
0.7983	Intermediate Similarity	NPC475913
0.7966	Intermediate Similarity	NPC243981
0.7951	Intermediate Similarity	NPC6193
0.7951	Intermediate Similarity	NPC27363
0.7951	Intermediate Similarity	NPC204812
0.7937	Intermediate Similarity	NPC471855
0.7934	Intermediate Similarity	NPC473256
0.7934	Intermediate Similarity	NPC67569
0.7934	Intermediate Similarity	NPC470878
0.792	Intermediate Similarity	NPC476966
0.7917	Intermediate Similarity	NPC5292
0.7917	Intermediate Similarity	NPC475520
0.7913	Intermediate Similarity	NPC112457
0.7903	Intermediate Similarity	NPC298841
0.7903	Intermediate Similarity	NPC42399
0.7899	Intermediate Similarity	NPC290693
0.7886	Intermediate Similarity	NPC469790
0.7869	Intermediate Similarity	NPC470265
0.7869	Intermediate Similarity	NPC23786
0.7857	Intermediate Similarity	NPC173347
0.7851	Intermediate Similarity	NPC474585
0.7851	Intermediate Similarity	NPC470312
0.7851	Intermediate Similarity	NPC474370
0.7851	Intermediate Similarity	NPC79579
0.784	Intermediate Similarity	NPC311534
0.7833	Intermediate Similarity	NPC113448
0.7833	Intermediate Similarity	NPC473720
0.7823	Intermediate Similarity	NPC250556
0.7823	Intermediate Similarity	NPC469750
0.7815	Intermediate Similarity	NPC176840
0.7805	Intermediate Similarity	NPC469789
0.7797	Intermediate Similarity	NPC471173
0.7797	Intermediate Similarity	NPC471627
0.7795	Intermediate Similarity	NPC155529
0.7788	Intermediate Similarity	NPC165608
0.7787	Intermediate Similarity	NPC46570
0.7787	Intermediate Similarity	NPC470418
0.7778	Intermediate Similarity	NPC104382
0.7778	Intermediate Similarity	NPC175186
0.7769	Intermediate Similarity	NPC475041
0.7769	Intermediate Similarity	NPC264954
0.7769	Intermediate Similarity	NPC305260
0.7769	Intermediate Similarity	NPC473274
0.7769	Intermediate Similarity	NPC270850
0.7769	Intermediate Similarity	NPC161065
0.776	Intermediate Similarity	NPC469757
0.776	Intermediate Similarity	NPC305496
0.776	Intermediate Similarity	NPC471357
0.776	Intermediate Similarity	NPC117702
0.776	Intermediate Similarity	NPC146456
0.776	Intermediate Similarity	NPC179412
0.776	Intermediate Similarity	NPC240070
0.776	Intermediate Similarity	NPC329784
0.776	Intermediate Similarity	NPC471356
0.7752	Intermediate Similarity	NPC158350
0.775	Intermediate Similarity	NPC13713
0.7742	Intermediate Similarity	NPC3381
0.7739	Intermediate Similarity	NPC180744
0.7731	Intermediate Similarity	NPC84949
0.7731	Intermediate Similarity	NPC31354
0.7731	Intermediate Similarity	NPC69576
0.7731	Intermediate Similarity	NPC477580
0.7731	Intermediate Similarity	NPC471633
0.7724	Intermediate Similarity	NPC107493
0.7724	Intermediate Similarity	NPC470419
0.7724	Intermediate Similarity	NPC170538
0.7717	Intermediate Similarity	NPC471170
0.7712	Intermediate Similarity	NPC236217
0.771	Intermediate Similarity	NPC75616
0.7705	Intermediate Similarity	NPC241192
0.7698	Intermediate Similarity	NPC245094
0.7692	Intermediate Similarity	NPC289700
0.7692	Intermediate Similarity	NPC62172
0.7692	Intermediate Similarity	NPC253906
0.7686	Intermediate Similarity	NPC473828
0.7686	Intermediate Similarity	NPC50774
0.7686	Intermediate Similarity	NPC473617
0.7686	Intermediate Similarity	NPC16701
0.7686	Intermediate Similarity	NPC709
0.768	Intermediate Similarity	NPC473635
0.768	Intermediate Similarity	NPC293112
0.768	Intermediate Similarity	NPC159499
0.7674	Intermediate Similarity	NPC478072
0.7667	Intermediate Similarity	NPC5311
0.7667	Intermediate Similarity	NPC302471
0.7667	Intermediate Similarity	NPC193382
0.7667	Intermediate Similarity	NPC199428
0.7667	Intermediate Similarity	NPC470793
0.7667	Intermediate Similarity	NPC310341
0.7667	Intermediate Similarity	NPC99620
0.7661	Intermediate Similarity	NPC11895
0.7658	Intermediate Similarity	NPC151488
0.7652	Intermediate Similarity	NPC477090
0.7652	Intermediate Similarity	NPC127790
0.7647	Intermediate Similarity	NPC157441
0.7642	Intermediate Similarity	NPC312481
0.7638	Intermediate Similarity	NPC188234
0.7638	Intermediate Similarity	NPC219085
0.7638	Intermediate Similarity	NPC70542
0.7638	Intermediate Similarity	NPC469755
0.7638	Intermediate Similarity	NPC232785
0.7638	Intermediate Similarity	NPC469753
0.7638	Intermediate Similarity	NPC276838
0.7638	Intermediate Similarity	NPC471358
0.7638	Intermediate Similarity	NPC471352
0.7638	Intermediate Similarity	NPC197707
0.7638	Intermediate Similarity	NPC471360
0.7638	Intermediate Similarity	NPC86159
0.7638	Intermediate Similarity	NPC471361
0.7638	Intermediate Similarity	NPC6108
0.7638	Intermediate Similarity	NPC329986
0.7638	Intermediate Similarity	NPC469751
0.7638	Intermediate Similarity	NPC471359
0.7638	Intermediate Similarity	NPC91
0.7638	Intermediate Similarity	NPC469752
0.7638	Intermediate Similarity	NPC9499
0.7638	Intermediate Similarity	NPC180079
0.7638	Intermediate Similarity	NPC140092
0.7638	Intermediate Similarity	NPC469754
0.7638	Intermediate Similarity	NPC125077
0.7638	Intermediate Similarity	NPC284406
0.7638	Intermediate Similarity	NPC10823
0.7638	Intermediate Similarity	NPC251866
0.7638	Intermediate Similarity	NPC17896
0.7638	Intermediate Similarity	NPC89514
0.7636	Intermediate Similarity	NPC281134
0.7636	Intermediate Similarity	NPC33473
0.7623	Intermediate Similarity	NPC29639
0.7623	Intermediate Similarity	NPC304260
0.7623	Intermediate Similarity	NPC153085
0.7623	Intermediate Similarity	NPC268326
0.7623	Intermediate Similarity	NPC473203
0.7623	Intermediate Similarity	NPC35171
0.7623	Intermediate Similarity	NPC477071
0.7623	Intermediate Similarity	NPC278681
0.7623	Intermediate Similarity	NPC5883
0.7623	Intermediate Similarity	NPC44899
0.7623	Intermediate Similarity	NPC473270
0.7623	Intermediate Similarity	NPC213761
0.7607	Intermediate Similarity	NPC469370
0.7603	Intermediate Similarity	NPC473852
0.7603	Intermediate Similarity	NPC286528
0.7603	Intermediate Similarity	NPC20302
0.7603	Intermediate Similarity	NPC243196
0.7603	Intermediate Similarity	NPC474418
0.7603	Intermediate Similarity	NPC152615
0.7603	Intermediate Similarity	NPC203862
0.7603	Intermediate Similarity	NPC142066
0.7603	Intermediate Similarity	NPC471351
0.7603	Intermediate Similarity	NPC77319
0.7603	Intermediate Similarity	NPC309034
0.7603	Intermediate Similarity	NPC84987
0.7603	Intermediate Similarity	NPC157376
0.7603	Intermediate Similarity	NPC244402
0.7603	Intermediate Similarity	NPC196429
0.7603	Intermediate Similarity	NPC470492
0.7603	Intermediate Similarity	NPC34390
0.7603	Intermediate Similarity	NPC471355
0.7603	Intermediate Similarity	NPC99728
0.7603	Intermediate Similarity	NPC50305
0.7603	Intermediate Similarity	NPC471353
0.7603	Intermediate Similarity	NPC167606
0.7603	Intermediate Similarity	NPC87250
0.7603	Intermediate Similarity	NPC140055
0.7603	Intermediate Similarity	NPC93883
0.7603	Intermediate Similarity	NPC471354
0.7603	Intermediate Similarity	NPC158344
0.7603	Intermediate Similarity	NPC157380
0.7603	Intermediate Similarity	NPC27507
0.76	Intermediate Similarity	NPC81736
0.76	Intermediate Similarity	NPC172154
0.76	Intermediate Similarity	NPC8369
0.7597	Intermediate Similarity	NPC157817
0.7597	Intermediate Similarity	NPC225385
0.7597	Intermediate Similarity	NPC104585
0.7597	Intermediate Similarity	NPC142756

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 NPC268213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	2086
0.2-0.3	3972
0.3-0.4	1926
0.4-0.5	498
0.5-0.6	234
0.6-0.7	149
0.7-0.8	28
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
0.7823	Intermediate Similarity	NPD7507	Approved
0.7652	Intermediate Similarity	NPD6008	Approved
0.7642	Intermediate Similarity	NPD7503	Approved
0.7638	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD7115	Discovery
0.7559	Intermediate Similarity	NPD7736	Approved
0.7541	Intermediate Similarity	NPD7328	Approved
0.7541	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.748	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD6009	Approved
0.7436	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD8294	Approved
0.7419	Intermediate Similarity	NPD8377	Approved
0.7373	Intermediate Similarity	NPD6686	Approved
0.736	Intermediate Similarity	NPD8380	Approved
0.736	Intermediate Similarity	NPD8379	Approved
0.736	Intermediate Similarity	NPD8296	Approved
0.736	Intermediate Similarity	NPD8378	Approved
0.736	Intermediate Similarity	NPD8335	Approved
0.7311	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6370	Approved
0.7281	Intermediate Similarity	NPD7638	Approved
0.725	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD7640	Approved
0.7213	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7132	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6015	Approved
0.7087	Intermediate Similarity	NPD6016	Approved
0.7077	Intermediate Similarity	NPD8293	Discontinued
0.7077	Intermediate Similarity	NPD7078	Approved
0.7073	Intermediate Similarity	NPD8133	Approved
0.7054	Intermediate Similarity	NPD5693	Phase 1
0.7031	Intermediate Similarity	NPD5988	Approved
0.7018	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD5697	Approved
0.6992	Remote Similarity	NPD8297	Approved
0.6977	Remote Similarity	NPD7604	Phase 2
0.6953	Remote Similarity	NPD5983	Phase 2
0.6942	Remote Similarity	NPD6899	Approved
0.6942	Remote Similarity	NPD6881	Approved
0.6942	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD6001	Approved
0.6909	Remote Similarity	NPD7521	Approved
0.6909	Remote Similarity	NPD6409	Approved
0.6909	Remote Similarity	NPD5330	Approved
0.6909	Remote Similarity	NPD7334	Approved
0.6909	Remote Similarity	NPD7146	Approved
0.6909	Remote Similarity	NPD6684	Approved
0.6885	Remote Similarity	NPD6012	Approved
0.6885	Remote Similarity	NPD6014	Approved
0.6885	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD6059	Approved
0.6829	Remote Similarity	NPD7290	Approved
0.6829	Remote Similarity	NPD6883	Approved
0.6829	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD1694	Approved
0.6807	Remote Similarity	NPD7632	Discontinued
0.6786	Remote Similarity	NPD6903	Approved
0.6777	Remote Similarity	NPD5739	Approved
0.6777	Remote Similarity	NPD7128	Approved
0.6777	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6402	Approved
0.6774	Remote Similarity	NPD8130	Phase 1
0.6774	Remote Similarity	NPD6869	Approved
0.6774	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD6650	Approved
0.6774	Remote Similarity	NPD6847	Approved
0.6774	Remote Similarity	NPD6617	Approved
0.6742	Remote Similarity	NPD6336	Discontinued
0.6726	Remote Similarity	NPD6673	Approved
0.6726	Remote Similarity	NPD6080	Approved
0.6726	Remote Similarity	NPD6904	Approved
0.6721	Remote Similarity	NPD5701	Approved
0.672	Remote Similarity	NPD6053	Discontinued
0.6718	Remote Similarity	NPD6067	Discontinued
0.6697	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6639	Remote Similarity	NPD6648	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6638	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7900	Approved
0.6637	Remote Similarity	NPD5208	Approved
0.6637	Remote Similarity	NPD5737	Approved
0.6637	Remote Similarity	NPD6672	Approved
0.6613	Remote Similarity	NPD6372	Approved
0.6613	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6373	Approved
0.661	Remote Similarity	NPD6083	Phase 2
0.661	Remote Similarity	NPD6084	Phase 2
0.6609	Remote Similarity	NPD5694	Approved
0.6591	Remote Similarity	NPD8328	Phase 3
0.6583	Remote Similarity	NPD5223	Approved
0.6583	Remote Similarity	NPD5344	Discontinued
0.6581	Remote Similarity	NPD5695	Phase 3
0.6579	Remote Similarity	NPD6051	Approved
0.656	Remote Similarity	NPD6371	Approved
0.656	Remote Similarity	NPD4634	Approved
0.6557	Remote Similarity	NPD5141	Approved
0.6555	Remote Similarity	NPD5696	Approved
0.6552	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD4202	Approved
0.6549	Remote Similarity	NPD3573	Approved
0.6529	Remote Similarity	NPD5225	Approved
0.6529	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD5226	Approved
0.6529	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD5692	Phase 3
0.6522	Remote Similarity	NPD5207	Approved
0.6519	Remote Similarity	NPD6033	Approved
0.6512	Remote Similarity	NPD6317	Approved
0.6508	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7748	Approved
0.6475	Remote Similarity	NPD5175	Approved
0.6475	Remote Similarity	NPD5174	Approved
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD7902	Approved
0.6466	Remote Similarity	NPD6050	Approved
0.6466	Remote Similarity	NPD5281	Approved
0.6466	Remote Similarity	NPD5284	Approved
0.6462	Remote Similarity	NPD6314	Approved
0.6462	Remote Similarity	NPD6335	Approved
0.6462	Remote Similarity	NPD6313	Approved
0.646	Remote Similarity	NPD6098	Approved
0.6439	Remote Similarity	NPD8513	Phase 3
0.6435	Remote Similarity	NPD1695	Approved
0.6434	Remote Similarity	NPD6274	Approved
0.6423	Remote Similarity	NPD5956	Approved
0.6417	Remote Similarity	NPD4225	Approved
0.6412	Remote Similarity	NPD7101	Approved
0.6412	Remote Similarity	NPD7100	Approved
0.64	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6333	Remote Similarity	NPD5959	Approved
0.6325	Remote Similarity	NPD7515	Phase 2
0.6325	Remote Similarity	NPD8035	Phase 2
0.6325	Remote Similarity	NPD8034	Phase 2
0.6325	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8515	Approved
0.6316	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8516	Approved
0.6316	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD4629	Approved
0.6303	Remote Similarity	NPD5654	Approved
0.6303	Remote Similarity	NPD5210	Approved
0.6293	Remote Similarity	NPD4753	Phase 2
0.629	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3665	Phase 1
0.6283	Remote Similarity	NPD3133	Approved
0.6283	Remote Similarity	NPD3666	Approved
0.627	Remote Similarity	NPD4730	Approved
0.627	Remote Similarity	NPD4729	Approved
0.6259	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6698	Approved
0.6239	Remote Similarity	NPD46	Approved
0.6235	Remote Similarity	NPD7799	Discontinued
0.6216	Remote Similarity	NPD7625	Phase 1
0.621	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD5173	Approved
0.619	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6614	Approved
0.6174	Remote Similarity	NPD3618	Phase 1
0.6174	Remote Similarity	NPD5690	Phase 2
0.6172	Remote Similarity	NPD5169	Approved
0.6172	Remote Similarity	NPD5251	Approved
0.6172	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5249	Phase 3
0.6172	Remote Similarity	NPD5250	Approved
0.6172	Remote Similarity	NPD5135	Approved
0.6172	Remote Similarity	NPD5247	Approved
0.6172	Remote Similarity	NPD5248	Approved
0.6159	Remote Similarity	NPD8336	Approved
0.6159	Remote Similarity	NPD8337	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6148	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5128	Approved
0.614	Remote Similarity	NPD4197	Approved
0.6124	Remote Similarity	NPD5216	Approved
0.6124	Remote Similarity	NPD5127	Approved
0.6124	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD5215	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