NPASS Compound

Structure

NPC475388 OpenBabel07101719142D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7196 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8286 -1.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3102 -0.9613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3376 -3.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3717 -2.9598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8823 -2.3800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8809 -2.3277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3194 -1.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -3.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4255 -3.1663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2529 -1.6029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 6 0 0 0 18 23 1 0 0 0 0 18 32 1 1 0 0 0 19 27 1 6 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 33 1 1 0 0 0 21 25 1 6 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 1 0 0 0 23 26 1 6 0 0 0 23 28 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 1 0 0 0 27 6 1 6 0 0 0 28 7 1 1 0 0 0 28 35 1 0 0 0 0 29 30 1 6 0 0 0 30 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	520.048
LogP:	4.097
LogD:	3.55
LogS:	-3.644
# Rotatable Bonds:	2
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	5.973
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083
MDCK Permeability:	1.3226841474534012e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	61.9285888671875%
Volume Distribution (VD):	0.871
Pgp-substrate:	15.494829177856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	7.464
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.909
Carcinogencity:	0.445
Eye Corrosion:	0.019
Eye Irritation:	0.018
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC475388

Natural Product ID:	NPC475388
*Common Name:**	WENNXORDXYGDTP-LLRAQJMZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WENNXORDXYGDTP-LLRAQJMZSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-24(2)20(33)8-11-30-16-29(30)13-12-26(5)23(28(7)10-9-21(35-28)25(3,4)34)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,22-,23+,26+,27-,28+,29-,30+/m0/s1
SMILES:	O[C@H]1C[C@@]2([C@]([C@@H]1[C@@]1(C)CC[C@H](O1)C(O)(C)C)(C)CC[C@@]13[C@H]2C[C@H](O)[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504655
PubChem CID:	44587060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO12927	Astragalus bicuspis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18771242]
NPO12927	Astragalus bicuspis	Species	Fabaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	100000.0	nM	PMID[543564]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	107570.0	nM	PMID[543564]

☑ 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 NPC475388 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	468
0.1-0.2	4497
0.2-0.3	14501
0.3-0.4	10155
0.4-0.5	5232
0.5-0.6	4792
0.6-0.7	2277
0.7-0.8	617
0.8-0.85	117
0.85-0.9	30
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC81074
0.9351	High Similarity	NPC477282
0.9342	High Similarity	NPC64081
0.9342	High Similarity	NPC474574
0.9342	High Similarity	NPC133596
0.9342	High Similarity	NPC11907
0.9103	High Similarity	NPC287452
0.9079	High Similarity	NPC317242
0.9079	High Similarity	NPC270306
0.9079	High Similarity	NPC91387
0.9079	High Similarity	NPC231680
0.8961	High Similarity	NPC470145
0.8961	High Similarity	NPC163597
0.8941	High Similarity	NPC473066
0.8929	High Similarity	NPC228059
0.8916	High Similarity	NPC161928
0.8916	High Similarity	NPC210658
0.8861	High Similarity	NPC269333
0.8846	High Similarity	NPC105208
0.8846	High Similarity	NPC185915
0.8846	High Similarity	NPC476233
0.8846	High Similarity	NPC477227
0.8846	High Similarity	NPC192046
0.8846	High Similarity	NPC128951
0.8846	High Similarity	NPC302578
0.8816	High Similarity	NPC470610
0.8816	High Similarity	NPC153719
0.881	High Similarity	NPC128475
0.8765	High Similarity	NPC470611
0.875	High Similarity	NPC16449
0.8736	High Similarity	NPC30687
0.8736	High Similarity	NPC175
0.8734	High Similarity	NPC147993
0.8734	High Similarity	NPC67657
0.8734	High Similarity	NPC18857
0.8701	High Similarity	NPC304499
0.8701	High Similarity	NPC48795
0.8659	High Similarity	NPC470070
0.8659	High Similarity	NPC477285
0.8659	High Similarity	NPC111582
0.8636	High Similarity	NPC473064
0.8636	High Similarity	NPC473067
0.8636	High Similarity	NPC473065
0.859	High Similarity	NPC243027
0.859	High Similarity	NPC472952
0.859	High Similarity	NPC472950
0.859	High Similarity	NPC196136
0.859	High Similarity	NPC158208
0.8571	High Similarity	NPC473238
0.8571	High Similarity	NPC155531
0.8571	High Similarity	NPC472341
0.8571	High Similarity	NPC215968
0.8571	High Similarity	NPC474448
0.8554	High Similarity	NPC320824
0.8553	High Similarity	NPC251201
0.8553	High Similarity	NPC232925
0.8553	High Similarity	NPC63588
0.8539	High Similarity	NPC156377
0.8539	High Similarity	NPC476510
0.8539	High Similarity	NPC142264
0.8537	High Similarity	NPC286719
0.8537	High Similarity	NPC477286
0.8506	High Similarity	NPC59006
0.85	High Similarity	NPC471769
0.8488	Intermediate Similarity	NPC20822
0.8471	Intermediate Similarity	NPC5943
0.8462	Intermediate Similarity	NPC192501
0.8462	Intermediate Similarity	NPC10476
0.8462	Intermediate Similarity	NPC228994
0.8452	Intermediate Similarity	NPC232044
0.8452	Intermediate Similarity	NPC273290
0.8452	Intermediate Similarity	NPC266651
0.8444	Intermediate Similarity	NPC233649
0.8444	Intermediate Similarity	NPC470028
0.8442	Intermediate Similarity	NPC187471
0.8442	Intermediate Similarity	NPC252182
0.8442	Intermediate Similarity	NPC1340
0.8442	Intermediate Similarity	NPC470071
0.8442	Intermediate Similarity	NPC131506
0.8442	Intermediate Similarity	NPC157777
0.8421	Intermediate Similarity	NPC66407
0.8421	Intermediate Similarity	NPC299948
0.8421	Intermediate Similarity	NPC241085
0.8421	Intermediate Similarity	NPC107919
0.8421	Intermediate Similarity	NPC477820
0.8421	Intermediate Similarity	NPC470830
0.8415	Intermediate Similarity	NPC190940
0.8409	Intermediate Similarity	NPC211845
0.8409	Intermediate Similarity	NPC256104
0.8409	Intermediate Similarity	NPC122083
0.8409	Intermediate Similarity	NPC311246
0.8409	Intermediate Similarity	NPC182740
0.8409	Intermediate Similarity	NPC167644
0.8391	Intermediate Similarity	NPC473542
0.8353	Intermediate Similarity	NPC477283
0.8353	Intermediate Similarity	NPC471240
0.8353	Intermediate Similarity	NPC131365
0.8333	Intermediate Similarity	NPC227260
0.8333	Intermediate Similarity	NPC474156
0.8315	Intermediate Similarity	NPC113500
0.8315	Intermediate Similarity	NPC252253
0.8315	Intermediate Similarity	NPC3538
0.8315	Intermediate Similarity	NPC477224
0.8315	Intermediate Similarity	NPC45959
0.8313	Intermediate Similarity	NPC296734
0.8313	Intermediate Similarity	NPC202688
0.8313	Intermediate Similarity	NPC154043
0.8313	Intermediate Similarity	NPC60018
0.8295	Intermediate Similarity	NPC149966
0.8295	Intermediate Similarity	NPC5632
0.8293	Intermediate Similarity	NPC66766
0.8293	Intermediate Similarity	NPC117137
0.8276	Intermediate Similarity	NPC82955
0.8272	Intermediate Similarity	NPC471045
0.8261	Intermediate Similarity	NPC470030
0.8256	Intermediate Similarity	NPC202937
0.8242	Intermediate Similarity	NPC475207
0.8235	Intermediate Similarity	NPC290612
0.8228	Intermediate Similarity	NPC475458
0.8214	Intermediate Similarity	NPC478054
0.8205	Intermediate Similarity	NPC8004
0.8205	Intermediate Similarity	NPC157422
0.8205	Intermediate Similarity	NPC100586
0.8205	Intermediate Similarity	NPC473279
0.8205	Intermediate Similarity	NPC109457
0.8205	Intermediate Similarity	NPC127094
0.8205	Intermediate Similarity	NPC127283
0.8205	Intermediate Similarity	NPC195530
0.8202	Intermediate Similarity	NPC88962
0.8202	Intermediate Similarity	NPC473726
0.8202	Intermediate Similarity	NPC144790
0.8202	Intermediate Similarity	NPC149400
0.8193	Intermediate Similarity	NPC473257
0.8182	Intermediate Similarity	NPC470833
0.8182	Intermediate Similarity	NPC279329
0.8172	Intermediate Similarity	NPC476512
0.8172	Intermediate Similarity	NPC472081
0.8172	Intermediate Similarity	NPC108227
0.8171	Intermediate Similarity	NPC476176
0.8161	Intermediate Similarity	NPC473436
0.8161	Intermediate Similarity	NPC56777
0.8161	Intermediate Similarity	NPC281004
0.8161	Intermediate Similarity	NPC201607
0.8158	Intermediate Similarity	NPC473230
0.8158	Intermediate Similarity	NPC63190
0.8158	Intermediate Similarity	NPC475884
0.8148	Intermediate Similarity	NPC171658
0.814	Intermediate Similarity	NPC103782
0.814	Intermediate Similarity	NPC114378
0.814	Intermediate Similarity	NPC80700
0.8132	Intermediate Similarity	NPC304011
0.8132	Intermediate Similarity	NPC116683
0.8132	Intermediate Similarity	NPC139271
0.8125	Intermediate Similarity	NPC131584
0.8125	Intermediate Similarity	NPC139765
0.8111	Intermediate Similarity	NPC291547
0.8111	Intermediate Similarity	NPC473851
0.8111	Intermediate Similarity	NPC174024
0.8111	Intermediate Similarity	NPC24960
0.8111	Intermediate Similarity	NPC475436
0.8111	Intermediate Similarity	NPC473774
0.8111	Intermediate Similarity	NPC179859
0.8111	Intermediate Similarity	NPC312678
0.8111	Intermediate Similarity	NPC253268
0.8111	Intermediate Similarity	NPC131693
0.809	Intermediate Similarity	NPC293609
0.809	Intermediate Similarity	NPC307167
0.809	Intermediate Similarity	NPC210759
0.809	Intermediate Similarity	NPC229801
0.809	Intermediate Similarity	NPC36372
0.8085	Intermediate Similarity	NPC470029
0.8085	Intermediate Similarity	NPC310138
0.8085	Intermediate Similarity	NPC114700
0.8085	Intermediate Similarity	NPC134967
0.8077	Intermediate Similarity	NPC192192
0.8077	Intermediate Similarity	NPC282454
0.8072	Intermediate Similarity	NPC472951
0.8072	Intermediate Similarity	NPC472943
0.8072	Intermediate Similarity	NPC7479
0.8072	Intermediate Similarity	NPC257296
0.8072	Intermediate Similarity	NPC248944
0.8068	Intermediate Similarity	NPC102725
0.8068	Intermediate Similarity	NPC473472
0.8052	Intermediate Similarity	NPC474756
0.8046	Intermediate Similarity	NPC140446
0.8046	Intermediate Similarity	NPC43912
0.8046	Intermediate Similarity	NPC472396
0.8043	Intermediate Similarity	NPC477223
0.8043	Intermediate Similarity	NPC477222
0.8026	Intermediate Similarity	NPC44122
0.8022	Intermediate Similarity	NPC474399
0.8022	Intermediate Similarity	NPC21897
0.8	Intermediate Similarity	NPC234352
0.8	Intermediate Similarity	NPC250393
0.8	Intermediate Similarity	NPC470151
0.8	Intermediate Similarity	NPC277774
0.8	Intermediate Similarity	NPC98193
0.8	Intermediate Similarity	NPC139181
0.8	Intermediate Similarity	NPC297348
0.8	Intermediate Similarity	NPC177834

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 NPC475388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	4396
0.2-0.3	3036
0.3-0.4	690
0.4-0.5	272
0.5-0.6	222
0.6-0.7	63
0.7-0.8	9
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
0.8421	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6928	Phase 2
0.8	Intermediate Similarity	NPD8171	Discontinued
0.7625	Intermediate Similarity	NPD4787	Phase 1
0.7209	Intermediate Similarity	NPD6697	Approved
0.7209	Intermediate Similarity	NPD6118	Approved
0.7209	Intermediate Similarity	NPD6115	Approved
0.7209	Intermediate Similarity	NPD6114	Approved
0.72	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6116	Phase 1
0.7089	Intermediate Similarity	NPD371	Approved
0.7045	Intermediate Similarity	NPD7525	Registered
0.6977	Remote Similarity	NPD6117	Approved
0.6907	Remote Similarity	NPD7991	Discontinued
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3703	Phase 2
0.6786	Remote Similarity	NPD4244	Approved
0.6786	Remote Similarity	NPD4245	Approved
0.6744	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7328	Approved
0.6577	Remote Similarity	NPD7327	Approved
0.6569	Remote Similarity	NPD1700	Approved
0.6548	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5360	Phase 3
0.6526	Remote Similarity	NPD7524	Approved
0.6518	Remote Similarity	NPD7516	Approved
0.6477	Remote Similarity	NPD3702	Approved
0.646	Remote Similarity	NPD8377	Approved
0.646	Remote Similarity	NPD8294	Approved
0.6408	Remote Similarity	NPD4159	Approved
0.6404	Remote Similarity	NPD8378	Approved
0.6404	Remote Similarity	NPD8296	Approved
0.6404	Remote Similarity	NPD8380	Approved
0.6404	Remote Similarity	NPD8033	Approved
0.6404	Remote Similarity	NPD8335	Approved
0.6404	Remote Similarity	NPD8379	Approved
0.6395	Remote Similarity	NPD4789	Approved
0.6383	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1810	Approved
0.6364	Remote Similarity	NPD1811	Approved
0.6327	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6700	Approved
0.6322	Remote Similarity	NPD5777	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6316	Remote Similarity	NPD6059	Approved
0.6304	Remote Similarity	NPD4748	Discontinued
0.6277	Remote Similarity	NPD6695	Phase 3
0.6263	Remote Similarity	NPD6702	Approved
0.6263	Remote Similarity	NPD6703	Approved
0.6263	Remote Similarity	NPD8035	Phase 2
0.6263	Remote Similarity	NPD8034	Phase 2
0.6222	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8133	Approved
0.6214	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD6370	Approved
0.6207	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7320	Approved
0.6196	Remote Similarity	NPD7645	Phase 2
0.619	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7507	Approved
0.6168	Remote Similarity	NPD7128	Approved
0.6168	Remote Similarity	NPD5739	Approved
0.6168	Remote Similarity	NPD6675	Approved
0.6168	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6146	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4758	Discontinued
0.6126	Remote Similarity	NPD8297	Approved
0.6121	Remote Similarity	NPD6016	Approved
0.6121	Remote Similarity	NPD6015	Approved
0.6117	Remote Similarity	NPD4755	Approved
0.6111	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD6942	Approved
0.6111	Remote Similarity	NPD7339	Approved
0.6105	Remote Similarity	NPD4788	Approved
0.6102	Remote Similarity	NPD7492	Approved
0.6091	Remote Similarity	NPD4634	Approved
0.6087	Remote Similarity	NPD3671	Phase 1
0.6087	Remote Similarity	NPD5364	Discontinued
0.6083	Remote Similarity	NPD7736	Approved
0.6082	Remote Similarity	NPD8308	Discontinued
0.6071	Remote Similarity	NPD4632	Approved
0.6068	Remote Similarity	NPD5988	Approved
0.6055	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD6899	Approved
0.605	Remote Similarity	NPD6616	Approved
0.6044	Remote Similarity	NPD6933	Approved
0.604	Remote Similarity	NPD4202	Approved
0.6038	Remote Similarity	NPD7632	Discontinued
0.6034	Remote Similarity	NPD6319	Approved
0.6033	Remote Similarity	NPD7319	Approved
0.6023	Remote Similarity	NPD2254	Approved
0.6023	Remote Similarity	NPD2686	Approved
0.6023	Remote Similarity	NPD2687	Approved
0.602	Remote Similarity	NPD7750	Discontinued
0.6019	Remote Similarity	NPD6008	Approved
0.6017	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5983	Remote Similarity	NPD7503	Approved
0.5977	Remote Similarity	NPD6705	Phase 1
0.5965	Remote Similarity	NPD6940	Discontinued
0.5963	Remote Similarity	NPD5701	Approved
0.5963	Remote Similarity	NPD5697	Approved
0.5957	Remote Similarity	NPD6931	Approved
0.5957	Remote Similarity	NPD6930	Phase 2
0.5955	Remote Similarity	NPD4243	Approved
0.5955	Remote Similarity	NPD6081	Approved
0.5946	Remote Similarity	NPD7102	Approved
0.5946	Remote Similarity	NPD7290	Approved
0.5946	Remote Similarity	NPD6883	Approved
0.5922	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8174	Phase 2
0.5893	Remote Similarity	NPD6847	Approved
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD6650	Approved
0.5888	Remote Similarity	NPD5211	Phase 2
0.5888	Remote Similarity	NPD5225	Approved
0.5888	Remote Similarity	NPD5226	Approved
0.5888	Remote Similarity	NPD5224	Approved
0.5888	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD6014	Approved
0.5856	Remote Similarity	NPD6013	Approved
0.5856	Remote Similarity	NPD6012	Approved
0.5851	Remote Similarity	NPD6929	Approved
0.5849	Remote Similarity	NPD8418	Phase 2
0.5841	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD5174	Approved
0.5833	Remote Similarity	NPD5175	Approved
0.5824	Remote Similarity	NPD4784	Approved
0.5824	Remote Similarity	NPD4785	Approved
0.5824	Remote Similarity	NPD6924	Approved
0.5824	Remote Similarity	NPD6926	Approved
0.582	Remote Similarity	NPD6033	Approved
0.581	Remote Similarity	NPD6083	Phase 2
0.581	Remote Similarity	NPD6084	Phase 2
0.5806	Remote Similarity	NPD6932	Approved
0.5794	Remote Similarity	NPD5223	Approved
0.5784	Remote Similarity	NPD7087	Discontinued
0.578	Remote Similarity	NPD5141	Approved
0.5776	Remote Similarity	NPD6009	Approved
0.5776	Remote Similarity	NPD7115	Discovery
0.5773	Remote Similarity	NPD3669	Approved
0.5773	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6011	Approved
0.5752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6067	Discontinued
0.5747	Remote Similarity	NPD4224	Phase 2
0.5743	Remote Similarity	NPD4753	Phase 2
0.5743	Remote Similarity	NPD5328	Approved
0.5729	Remote Similarity	NPD6902	Approved
0.5728	Remote Similarity	NPD6399	Phase 3
0.5727	Remote Similarity	NPD4768	Approved
0.5727	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4754	Approved
0.5684	Remote Similarity	NPD6683	Phase 2
0.5664	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7919	Phase 3
0.566	Remote Similarity	NPD7920	Phase 3
0.5658	Remote Similarity	NPD385	Approved
0.5658	Remote Similarity	NPD384	Approved
0.5657	Remote Similarity	NPD6893	Approved
0.5656	Remote Similarity	NPD6336	Discontinued
0.5638	Remote Similarity	NPD6925	Approved
0.5638	Remote Similarity	NPD5776	Phase 2
0.5631	Remote Similarity	NPD6079	Approved
0.5625	Remote Similarity	NPD4729	Approved
0.5625	Remote Similarity	NPD4730	Approved
0.5625	Remote Similarity	NPD7514	Phase 3
0.5625	Remote Similarity	NPD5128	Approved
0.5625	Remote Similarity	NPD7509	Discontinued
0.5607	Remote Similarity	NPD4225	Approved
0.5607	Remote Similarity	NPD8088	Phase 1
0.56	Remote Similarity	NPD3618	Phase 1

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