NPASS Compound

Structure

NPC63897 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 3.0029 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 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 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 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 -0.0000 -3.0000 0.0000 O 0 0 0 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 2.5981 -1.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 4 8 1 0 0 0 0 4 17 2 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 22 1 0 0 0 0 7 1 1 6 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 9 3 1 6 0 0 0 9 11 1 0 0 0 0 10 5 1 1 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.15
Volume:	324.672
LogP:	0.204
LogD:	0.719
LogS:	-1.64
# Rotatable Bonds:	4
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.765
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.702
MDCK Permeability:	7.878972974140197e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.313
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	31.030376434326172%
Volume Distribution (VD):	0.633
Pgp-substrate:	50.83082962036133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.633
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	1.441
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.312
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.405
Carcinogencity:	0.945
Eye Corrosion:	0.009
Eye Irritation:	0.22
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC63897

Natural Product ID:	NPC63897
*Common Name:**	Boschnaloside
IUPAC Name:	(1S,4aS,7R,7aR)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carbaldehyde
Synonyms:
Standard InCHIKey:	MRIFZKMKTDPBHR-XLOWEYQUSA-N
Standard InCHI:	InChI=1S/C16H24O8/c1-7-2-3-9-8(4-17)6-22-15(11(7)9)24-16-14(21)13(20)12(19)10(5-18)23-16/h4,6-7,9-16,18-21H,2-3,5H2,1H3/t7-,9-,10-,11-,12-,13+,14-,15+,16+/m1/s1
SMILES:	O=CC1=CO[C@H]([C@H]2[C@@H]1CC[C@H]2C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622813
PubChem CID:	155942
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	43.0	%	PMID[483608]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	48.0	%	PMID[483608]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	73.3	%	PMID[483608]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[483608]

☑ 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 NPC63897 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	195
0.1-0.2	1469
0.2-0.3	5939
0.3-0.4	12929
0.4-0.5	10012
0.5-0.6	8652
0.6-0.7	3264
0.7-0.8	215
0.8-0.85	3
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9255	High Similarity	NPC304163
0.914	High Similarity	NPC37866
0.8947	High Similarity	NPC3488
0.8947	High Similarity	NPC287539
0.8854	High Similarity	NPC106668
0.8854	High Similarity	NPC4899
0.8854	High Similarity	NPC177013
0.8854	High Similarity	NPC474730
0.8854	High Similarity	NPC35185
0.8763	High Similarity	NPC27687
0.8763	High Similarity	NPC475928
0.8763	High Similarity	NPC37240
0.8723	High Similarity	NPC161293
0.8586	High Similarity	NPC127235
0.8586	High Similarity	NPC170432
0.85	High Similarity	NPC80338
0.85	High Similarity	NPC148270
0.85	High Similarity	NPC197813
0.8252	Intermediate Similarity	NPC193741
0.8235	Intermediate Similarity	NPC110701
0.8095	Intermediate Similarity	NPC475924
0.8095	Intermediate Similarity	NPC475851
0.8	Intermediate Similarity	NPC65665
0.8	Intermediate Similarity	NPC216826
0.8	Intermediate Similarity	NPC470573
0.8	Intermediate Similarity	NPC120021
0.8	Intermediate Similarity	NPC270908
0.8	Intermediate Similarity	NPC231710
0.7959	Intermediate Similarity	NPC241911
0.79	Intermediate Similarity	NPC255677
0.79	Intermediate Similarity	NPC306344
0.79	Intermediate Similarity	NPC22149
0.79	Intermediate Similarity	NPC473146
0.7879	Intermediate Similarity	NPC263674
0.7879	Intermediate Similarity	NPC261372
0.7879	Intermediate Similarity	NPC58267
0.7864	Intermediate Similarity	NPC41681
0.7857	Intermediate Similarity	NPC93869
0.7857	Intermediate Similarity	NPC6765
0.7822	Intermediate Similarity	NPC298255
0.7822	Intermediate Similarity	NPC28304
0.7812	Intermediate Similarity	NPC117596
0.78	Intermediate Similarity	NPC472015
0.78	Intermediate Similarity	NPC249171
0.78	Intermediate Similarity	NPC49833
0.7778	Intermediate Similarity	NPC474297
0.7755	Intermediate Similarity	NPC274588
0.7745	Intermediate Similarity	NPC222062
0.7745	Intermediate Similarity	NPC261117
0.7745	Intermediate Similarity	NPC80144
0.7745	Intermediate Similarity	NPC310804
0.7745	Intermediate Similarity	NPC94919
0.7732	Intermediate Similarity	NPC472125
0.7732	Intermediate Similarity	NPC472124
0.7732	Intermediate Similarity	NPC472126
0.7732	Intermediate Similarity	NPC235051
0.7708	Intermediate Similarity	NPC50464
0.77	Intermediate Similarity	NPC304445
0.77	Intermediate Similarity	NPC236580
0.767	Intermediate Similarity	NPC197541
0.767	Intermediate Similarity	NPC284929
0.767	Intermediate Similarity	NPC118761
0.767	Intermediate Similarity	NPC267869
0.767	Intermediate Similarity	NPC234304
0.767	Intermediate Similarity	NPC473148
0.7653	Intermediate Similarity	NPC61201
0.7647	Intermediate Similarity	NPC67296
0.7642	Intermediate Similarity	NPC8431
0.7629	Intermediate Similarity	NPC307699
0.7615	Intermediate Similarity	NPC74727
0.76	Intermediate Similarity	NPC170527
0.7596	Intermediate Similarity	NPC86095
0.7579	Intermediate Similarity	NPC470657
0.7573	Intermediate Similarity	NPC250545
0.7553	Intermediate Similarity	NPC259296
0.7553	Intermediate Similarity	NPC98276
0.7547	Intermediate Similarity	NPC230888
0.7526	Intermediate Similarity	NPC93190
0.7525	Intermediate Similarity	NPC472290
0.7525	Intermediate Similarity	NPC476613
0.7525	Intermediate Similarity	NPC278506
0.7525	Intermediate Similarity	NPC476612
0.7524	Intermediate Similarity	NPC210178
0.75	Intermediate Similarity	NPC274833
0.75	Intermediate Similarity	NPC31349
0.75	Intermediate Similarity	NPC108141
0.7477	Intermediate Similarity	NPC246205
0.7477	Intermediate Similarity	NPC118225
0.7476	Intermediate Similarity	NPC216911
0.7476	Intermediate Similarity	NPC476611
0.7453	Intermediate Similarity	NPC287269
0.7451	Intermediate Similarity	NPC56071
0.7451	Intermediate Similarity	NPC70733
0.7449	Intermediate Similarity	NPC303451
0.7449	Intermediate Similarity	NPC6414
0.7431	Intermediate Similarity	NPC207845
0.7431	Intermediate Similarity	NPC472719
0.7429	Intermediate Similarity	NPC264584
0.7426	Intermediate Similarity	NPC284063
0.7404	Intermediate Similarity	NPC195510
0.7404	Intermediate Similarity	NPC13171
0.7387	Intermediate Similarity	NPC31797
0.7383	Intermediate Similarity	NPC224414
0.7383	Intermediate Similarity	NPC88744
0.7379	Intermediate Similarity	NPC476320
0.7379	Intermediate Similarity	NPC476211
0.7374	Intermediate Similarity	NPC473150
0.7374	Intermediate Similarity	NPC294643
0.7374	Intermediate Similarity	NPC274274
0.7368	Intermediate Similarity	NPC42675
0.7364	Intermediate Similarity	NPC73986
0.7353	Intermediate Similarity	NPC86843
0.7347	Intermediate Similarity	NPC22918
0.7339	Intermediate Similarity	NPC122339
0.7339	Intermediate Similarity	NPC63244
0.7333	Intermediate Similarity	NPC329834
0.7327	Intermediate Similarity	NPC101051
0.7327	Intermediate Similarity	NPC167893
0.7315	Intermediate Similarity	NPC51947
0.7315	Intermediate Similarity	NPC473844
0.7315	Intermediate Similarity	NPC240125
0.7315	Intermediate Similarity	NPC91583
0.7308	Intermediate Similarity	NPC476230
0.7308	Intermediate Similarity	NPC27474
0.7304	Intermediate Similarity	NPC216866
0.7273	Intermediate Similarity	NPC157929
0.7273	Intermediate Similarity	NPC145625
0.7273	Intermediate Similarity	NPC471244
0.7273	Intermediate Similarity	NPC471245
0.7273	Intermediate Similarity	NPC473303
0.7264	Intermediate Similarity	NPC223741
0.7264	Intermediate Similarity	NPC121566
0.7264	Intermediate Similarity	NPC100955
0.7257	Intermediate Similarity	NPC13710
0.7255	Intermediate Similarity	NPC54731
0.7255	Intermediate Similarity	NPC256230
0.7255	Intermediate Similarity	NPC306041
0.725	Intermediate Similarity	NPC155529
0.7248	Intermediate Similarity	NPC106760
0.7248	Intermediate Similarity	NPC475317
0.7248	Intermediate Similarity	NPC154856
0.7248	Intermediate Similarity	NPC114961
0.7248	Intermediate Similarity	NPC471476
0.7248	Intermediate Similarity	NPC473324
0.7248	Intermediate Similarity	NPC52241
0.7248	Intermediate Similarity	NPC27551
0.7248	Intermediate Similarity	NPC129340
0.7245	Intermediate Similarity	NPC148534
0.7241	Intermediate Similarity	NPC1980
0.7241	Intermediate Similarity	NPC238005
0.7241	Intermediate Similarity	NPC141196
0.7232	Intermediate Similarity	NPC137414
0.7232	Intermediate Similarity	NPC88945
0.7232	Intermediate Similarity	NPC472718
0.7222	Intermediate Similarity	NPC295389
0.7222	Intermediate Similarity	NPC195708
0.7222	Intermediate Similarity	NPC177524
0.7222	Intermediate Similarity	NPC473288
0.7222	Intermediate Similarity	NPC219900
0.7222	Intermediate Similarity	NPC392
0.7216	Intermediate Similarity	NPC171484
0.7216	Intermediate Similarity	NPC149018
0.7207	Intermediate Similarity	NPC260665
0.7207	Intermediate Similarity	NPC94141
0.7207	Intermediate Similarity	NPC132668
0.7207	Intermediate Similarity	NPC477944
0.72	Intermediate Similarity	NPC66504
0.72	Intermediate Similarity	NPC472197
0.7196	Intermediate Similarity	NPC307660
0.7196	Intermediate Similarity	NPC162033
0.7196	Intermediate Similarity	NPC95243
0.7196	Intermediate Similarity	NPC130511
0.7196	Intermediate Similarity	NPC63023
0.7188	Intermediate Similarity	NPC475963
0.7188	Intermediate Similarity	NPC3464
0.7188	Intermediate Similarity	NPC151176
0.7184	Intermediate Similarity	NPC470684
0.7184	Intermediate Similarity	NPC470683
0.7182	Intermediate Similarity	NPC250481
0.7182	Intermediate Similarity	NPC275668
0.7182	Intermediate Similarity	NPC11035
0.7182	Intermediate Similarity	NPC240734
0.7182	Intermediate Similarity	NPC91838
0.7182	Intermediate Similarity	NPC272242
0.7182	Intermediate Similarity	NPC285410
0.7182	Intermediate Similarity	NPC263827
0.7182	Intermediate Similarity	NPC204392
0.7182	Intermediate Similarity	NPC1876
0.7179	Intermediate Similarity	NPC190846
0.7179	Intermediate Similarity	NPC277191
0.717	Intermediate Similarity	NPC329704
0.7168	Intermediate Similarity	NPC473304
0.7157	Intermediate Similarity	NPC469543
0.7156	Intermediate Similarity	NPC131903
0.7156	Intermediate Similarity	NPC265655
0.7155	Intermediate Similarity	NPC475431
0.7143	Intermediate Similarity	NPC165439
0.7143	Intermediate Similarity	NPC476228
0.7143	Intermediate Similarity	NPC471401
0.7143	Intermediate Similarity	NPC258501

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 NPC63897 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	2122
0.2-0.3	4178
0.3-0.4	1782
0.4-0.5	474
0.5-0.6	362
0.6-0.7	52
0.7-0.8	1
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
0.729	Intermediate Similarity	NPD6412	Phase 2
0.7222	Intermediate Similarity	NPD6686	Approved
0.6975	Remote Similarity	NPD7507	Approved
0.6903	Remote Similarity	NPD8133	Approved
0.6803	Remote Similarity	NPD7319	Approved
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD7641	Discontinued
0.6639	Remote Similarity	NPD7503	Approved
0.6583	Remote Similarity	NPD6370	Approved
0.65	Remote Similarity	NPD8513	Phase 3
0.6486	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6054	Approved
0.6404	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7736	Approved
0.6311	Remote Similarity	NPD5988	Approved
0.6311	Remote Similarity	NPD8080	Discontinued
0.6303	Remote Similarity	NPD6009	Approved
0.63	Remote Similarity	NPD6435	Approved
0.6281	Remote Similarity	NPD6059	Approved
0.6281	Remote Similarity	NPD6319	Approved
0.6262	Remote Similarity	NPD5282	Discontinued
0.626	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD7328	Approved
0.625	Remote Similarity	NPD7327	Approved
0.624	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD6882	Approved
0.623	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4249	Approved
0.621	Remote Similarity	NPD7492	Approved
0.6198	Remote Similarity	NPD7516	Approved
0.6186	Remote Similarity	NPD4632	Approved
0.6167	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6616	Approved
0.6154	Remote Similarity	NPD4251	Approved
0.6154	Remote Similarity	NPD4250	Approved
0.6148	Remote Similarity	NPD8294	Approved
0.6148	Remote Similarity	NPD8377	Approved
0.6129	Remote Similarity	NPD7830	Approved
0.6129	Remote Similarity	NPD7642	Approved
0.6129	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD7078	Approved
0.6102	Remote Similarity	NPD8297	Approved
0.61	Remote Similarity	NPD5368	Approved
0.6098	Remote Similarity	NPD8380	Approved
0.6098	Remote Similarity	NPD8296	Approved
0.6098	Remote Similarity	NPD8379	Approved
0.6098	Remote Similarity	NPD8335	Approved
0.6098	Remote Similarity	NPD8378	Approved
0.6098	Remote Similarity	NPD8033	Approved
0.6087	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8340	Approved
0.608	Remote Similarity	NPD8341	Approved
0.608	Remote Similarity	NPD8342	Approved
0.608	Remote Similarity	NPD8299	Approved
0.6078	Remote Similarity	NPD7154	Phase 3
0.6078	Remote Similarity	NPD4788	Approved
0.6063	Remote Similarity	NPD8336	Approved
0.6063	Remote Similarity	NPD8337	Approved
0.6053	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3181	Approved
0.6032	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD7839	Suspended
0.5984	Remote Similarity	NPD8448	Approved
0.5981	Remote Similarity	NPD7838	Discovery
0.5948	Remote Similarity	NPD5697	Approved
0.5932	Remote Similarity	NPD4634	Approved
0.5932	Remote Similarity	NPD6371	Approved
0.5926	Remote Similarity	NPD8035	Phase 2
0.5926	Remote Similarity	NPD8034	Phase 2
0.5922	Remote Similarity	NPD5362	Discontinued
0.5922	Remote Similarity	NPD6110	Phase 1
0.5897	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5888	Remote Similarity	NPD6101	Approved
0.5888	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD6650	Approved
0.5878	Remote Similarity	NPD8338	Approved
0.5877	Remote Similarity	NPD8138	Approved
0.5877	Remote Similarity	NPD8086	Approved
0.5877	Remote Similarity	NPD8139	Approved
0.5877	Remote Similarity	NPD8083	Approved
0.5877	Remote Similarity	NPD8082	Approved
0.5877	Remote Similarity	NPD8085	Approved
0.5877	Remote Similarity	NPD8084	Approved
0.5872	Remote Similarity	NPD8171	Discontinued
0.5872	Remote Similarity	NPD5779	Approved
0.5872	Remote Similarity	NPD5778	Approved
0.5872	Remote Similarity	NPD6399	Phase 3
0.5862	Remote Similarity	NPD7128	Approved
0.5862	Remote Similarity	NPD6402	Approved
0.5862	Remote Similarity	NPD6675	Approved
0.5862	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD8074	Phase 3
0.5856	Remote Similarity	NPD4697	Phase 3
0.5849	Remote Similarity	NPD7524	Approved
0.5847	Remote Similarity	NPD6372	Approved
0.5847	Remote Similarity	NPD6014	Approved
0.5847	Remote Similarity	NPD6013	Approved
0.5847	Remote Similarity	NPD6012	Approved
0.5847	Remote Similarity	NPD6373	Approved
0.5846	Remote Similarity	NPD8391	Approved
0.5846	Remote Similarity	NPD8390	Approved
0.5846	Remote Similarity	NPD5956	Approved
0.5846	Remote Similarity	NPD8392	Approved
0.5841	Remote Similarity	NPD4696	Approved
0.5841	Remote Similarity	NPD5286	Approved
0.5841	Remote Similarity	NPD5285	Approved
0.584	Remote Similarity	NPD8266	Approved
0.584	Remote Similarity	NPD5983	Phase 2
0.584	Remote Similarity	NPD8444	Approved
0.584	Remote Similarity	NPD8269	Approved
0.584	Remote Similarity	NPD8268	Approved
0.584	Remote Similarity	NPD8267	Approved
0.5826	Remote Similarity	NPD8276	Approved
0.5826	Remote Similarity	NPD8275	Approved
0.5814	Remote Similarity	NPD6033	Approved
0.5812	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.581	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6084	Phase 2
0.5804	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD4755	Approved
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6079	Approved
0.578	Remote Similarity	NPD7637	Suspended
0.578	Remote Similarity	NPD6411	Approved
0.5776	Remote Similarity	NPD8081	Approved
0.5772	Remote Similarity	NPD7115	Discovery
0.5769	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3669	Approved
0.5766	Remote Similarity	NPD5695	Phase 3
0.5763	Remote Similarity	NPD7320	Approved
0.5763	Remote Similarity	NPD6011	Approved
0.5763	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5279	Phase 3
0.5752	Remote Similarity	NPD7638	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD6617	Approved
0.5748	Remote Similarity	NPD7122	Discontinued
0.5748	Remote Similarity	NPD7604	Phase 2
0.5743	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4238	Approved
0.5743	Remote Similarity	NPD4802	Phase 2
0.5741	Remote Similarity	NPD4753	Phase 2
0.5741	Remote Similarity	NPD1695	Approved
0.5741	Remote Similarity	NPD5328	Approved
0.5739	Remote Similarity	NPD5226	Approved
0.5739	Remote Similarity	NPD5225	Approved
0.5739	Remote Similarity	NPD5224	Approved
0.5739	Remote Similarity	NPD4633	Approved
0.5739	Remote Similarity	NPD5211	Phase 2
0.5728	Remote Similarity	NPD5369	Approved
0.5728	Remote Similarity	NPD1779	Approved
0.5728	Remote Similarity	NPD1780	Approved
0.5726	Remote Similarity	NPD8393	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD5221	Approved
0.5714	Remote Similarity	NPD3666	Approved
0.5704	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD4700	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.5691	Remote Similarity	NPD6940	Discontinued
0.569	Remote Similarity	NPD5175	Approved
0.569	Remote Similarity	NPD5174	Approved
0.5684	Remote Similarity	NPD896	Approved
0.5684	Remote Similarity	NPD898	Approved
0.5684	Remote Similarity	NPD897	Approved
0.5678	Remote Similarity	NPD8307	Discontinued
0.5678	Remote Similarity	NPD8140	Approved
0.5673	Remote Similarity	NPD3667	Approved
0.567	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5173	Approved
0.566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5363	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