NPASS Compound

Structure

CID296620 OpenBabel06191716102D 26 30 0 0 1 0 0 0 0 0999 V2000 2.8345 -1.9054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1490 0.4106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9828 0.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8646 -1.6222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9007 -0.9047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7734 -3.1252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5466 -1.7858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7733 -0.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9931 -1.9054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5466 -2.6787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0001 -2.6787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2811 -2.0412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6548 -0.5535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6662 -1.3393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0335 -0.1561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3623 -0.4291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7732 -1.3394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7733 -1.3393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7733 -0.4464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7286 -3.0994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2228 -2.9056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0869 -0.6106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0313 0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6350 -0.3575 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 9 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 17 1 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 19 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 6 1 6 0 0 0 11 13 1 0 0 0 0 11 21 1 1 0 0 0 12 18 1 1 0 0 0 12 22 1 0 0 0 0 13 18 1 1 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 1 0 0 0 15 19 1 6 0 0 0 15 23 1 0 0 0 0 16 20 1 6 0 0 0 16 24 1 0 0 0 0 18 8 1 1 0 0 0 19 20 1 1 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.2
Volume:	361.799
LogP:	1.269
LogD:	0.779
LogS:	-3.925
# Rotatable Bonds:	0
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	7.145
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.018
MDCK Permeability:	9.264726941182744e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.386
30% Bioavailability (F30%):	0.265

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	51.23529052734375%
Volume Distribution (VD):	0.768
Pgp-substrate:	65.37699890136719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.61
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.806
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.641
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.24
Carcinogencity:	0.501
Eye Corrosion:	0.005
Eye Irritation:	0.021
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC296620

Natural Product ID:	NPC296620
*Common Name:**	Nervosanin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DSHJJLKUJOADCV-OIAFLBERSA-N
Standard InCHI:	InChI=1S/C20H30O6/c1-9-10-6-11(21)13-18-8-26-20(25,19(13,7-10)15(9)23)16(24)14(18)17(2,3)5-4-12(18)22/h10-16,21-25H,1,4-8H2,2-3H3/t10-,11-,12+,13+,14-,15-,16+,18+,19+,20+/m1/s1
SMILES:	C=C1[C@@H]2C[C@H]([C@H]3[C@]45CO[C@@]([C@H]([C@@H]5C(C)(C)CC[C@@H]4O)O)([C@]3(C2)[C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079533
PubChem CID:	46883376
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO3176	Rabdosia nervosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3176	Rabdosia nervosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3176	Rabdosia nervosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3176	Rabdosia nervosa	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[523643]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[523643]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[523643]

☑ 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 NPC296620 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	268
0.1-0.2	2362
0.2-0.3	7184
0.3-0.4	14296
0.4-0.5	8175
0.5-0.6	4781
0.6-0.7	3416
0.7-0.8	1785
0.8-0.85	350
0.85-0.9	56
0.9-0.95	15
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC473348
0.9551	High Similarity	NPC30477
0.9451	High Similarity	NPC469725
0.9247	High Similarity	NPC144486
0.9247	High Similarity	NPC470168
0.914	High Similarity	NPC471242
0.914	High Similarity	NPC471247
0.914	High Similarity	NPC91497
0.8947	High Similarity	NPC31085
0.8925	High Similarity	NPC76486
0.8854	High Similarity	NPC471467
0.8791	High Similarity	NPC469738
0.8776	High Similarity	NPC470166
0.8763	High Similarity	NPC152966
0.875	High Similarity	NPC177701
0.8646	High Similarity	NPC31346
0.8617	High Similarity	NPC111834
0.8617	High Similarity	NPC292718
0.8617	High Similarity	NPC306797
0.8617	High Similarity	NPC169270
0.8586	High Similarity	NPC470169
0.8586	High Similarity	NPC470170
0.8571	High Similarity	NPC475521
0.8557	High Similarity	NPC52585
0.8557	High Similarity	NPC68630
0.8557	High Similarity	NPC228049
0.8511	High Similarity	NPC241047
0.8511	High Similarity	NPC476894
0.8438	Intermediate Similarity	NPC476895
0.8431	Intermediate Similarity	NPC56025
0.8421	Intermediate Similarity	NPC472989
0.84	Intermediate Similarity	NPC54619
0.8333	Intermediate Similarity	NPC476893
0.8333	Intermediate Similarity	NPC274793
0.8317	Intermediate Similarity	NPC476513
0.83	Intermediate Similarity	NPC242748
0.8283	Intermediate Similarity	NPC473198
0.8283	Intermediate Similarity	NPC16573
0.8283	Intermediate Similarity	NPC475701
0.828	Intermediate Similarity	NPC219937
0.828	Intermediate Similarity	NPC123252
0.828	Intermediate Similarity	NPC194485
0.828	Intermediate Similarity	NPC53890
0.8265	Intermediate Similarity	NPC476896
0.8265	Intermediate Similarity	NPC471112
0.8261	Intermediate Similarity	NPC160304
0.8247	Intermediate Similarity	NPC234287
0.8247	Intermediate Similarity	NPC280825
0.8242	Intermediate Similarity	NPC471240
0.8235	Intermediate Similarity	NPC474573
0.8235	Intermediate Similarity	NPC151134
0.8235	Intermediate Similarity	NPC473570
0.8222	Intermediate Similarity	NPC255882
0.8218	Intermediate Similarity	NPC231340
0.8218	Intermediate Similarity	NPC473469
0.82	Intermediate Similarity	NPC312774
0.82	Intermediate Similarity	NPC474464
0.82	Intermediate Similarity	NPC75608
0.82	Intermediate Similarity	NPC273879
0.82	Intermediate Similarity	NPC476361
0.82	Intermediate Similarity	NPC165033
0.82	Intermediate Similarity	NPC476360
0.8191	Intermediate Similarity	NPC48463
0.8182	Intermediate Similarity	NPC288694
0.8182	Intermediate Similarity	NPC312553
0.8182	Intermediate Similarity	NPC159036
0.8163	Intermediate Similarity	NPC473200
0.8163	Intermediate Similarity	NPC317019
0.8163	Intermediate Similarity	NPC7341
0.8155	Intermediate Similarity	NPC470867
0.8137	Intermediate Similarity	NPC7213
0.8137	Intermediate Similarity	NPC89860
0.8137	Intermediate Similarity	NPC475634
0.8137	Intermediate Similarity	NPC51172
0.8137	Intermediate Similarity	NPC189663
0.8137	Intermediate Similarity	NPC49032
0.8137	Intermediate Similarity	NPC125324
0.8119	Intermediate Similarity	NPC473923
0.8119	Intermediate Similarity	NPC165405
0.8119	Intermediate Similarity	NPC472898
0.8119	Intermediate Similarity	NPC472900
0.8119	Intermediate Similarity	NPC473476
0.8119	Intermediate Similarity	NPC130511
0.8119	Intermediate Similarity	NPC474015
0.8119	Intermediate Similarity	NPC472899
0.8119	Intermediate Similarity	NPC307660
0.8105	Intermediate Similarity	NPC26046
0.81	Intermediate Similarity	NPC245280
0.81	Intermediate Similarity	NPC211879
0.81	Intermediate Similarity	NPC8039
0.81	Intermediate Similarity	NPC157659
0.81	Intermediate Similarity	NPC120123
0.81	Intermediate Similarity	NPC31907
0.81	Intermediate Similarity	NPC189852
0.81	Intermediate Similarity	NPC155010
0.81	Intermediate Similarity	NPC16520
0.81	Intermediate Similarity	NPC114874
0.81	Intermediate Similarity	NPC286969
0.81	Intermediate Similarity	NPC472252
0.81	Intermediate Similarity	NPC131479
0.81	Intermediate Similarity	NPC473020
0.8095	Intermediate Similarity	NPC307642
0.8081	Intermediate Similarity	NPC88000
0.8081	Intermediate Similarity	NPC129372
0.8081	Intermediate Similarity	NPC470434
0.8081	Intermediate Similarity	NPC160734
0.8081	Intermediate Similarity	NPC4831
0.8081	Intermediate Similarity	NPC472023
0.8081	Intermediate Similarity	NPC309425
0.8081	Intermediate Similarity	NPC49532
0.8081	Intermediate Similarity	NPC47566
0.8068	Intermediate Similarity	NPC24504
0.8068	Intermediate Similarity	NPC476316
0.8065	Intermediate Similarity	NPC473436
0.8061	Intermediate Similarity	NPC275865
0.8058	Intermediate Similarity	NPC102741
0.8058	Intermediate Similarity	NPC118721
0.8058	Intermediate Similarity	NPC252679
0.8058	Intermediate Similarity	NPC128133
0.8043	Intermediate Similarity	NPC121981
0.8041	Intermediate Similarity	NPC90583
0.8039	Intermediate Similarity	NPC67745
0.8039	Intermediate Similarity	NPC181467
0.8039	Intermediate Similarity	NPC471461
0.8022	Intermediate Similarity	NPC256567
0.8021	Intermediate Similarity	NPC305160
0.802	Intermediate Similarity	NPC221562
0.802	Intermediate Similarity	NPC470885
0.802	Intermediate Similarity	NPC471111
0.802	Intermediate Similarity	NPC475365
0.802	Intermediate Similarity	NPC187400
0.8	Intermediate Similarity	NPC289361
0.8	Intermediate Similarity	NPC219516
0.8	Intermediate Similarity	NPC473567
0.8	Intermediate Similarity	NPC136816
0.8	Intermediate Similarity	NPC477050
0.8	Intermediate Similarity	NPC130840
0.8	Intermediate Similarity	NPC216595
0.8	Intermediate Similarity	NPC22634
0.7981	Intermediate Similarity	NPC141433
0.7981	Intermediate Similarity	NPC471476
0.798	Intermediate Similarity	NPC64348
0.798	Intermediate Similarity	NPC469942
0.798	Intermediate Similarity	NPC473790
0.7979	Intermediate Similarity	NPC473472
0.7978	Intermediate Similarity	NPC47149
0.7961	Intermediate Similarity	NPC476540
0.7961	Intermediate Similarity	NPC55973
0.7961	Intermediate Similarity	NPC476541
0.7961	Intermediate Similarity	NPC473517
0.7961	Intermediate Similarity	NPC246124
0.7961	Intermediate Similarity	NPC473410
0.7961	Intermediate Similarity	NPC471094
0.7961	Intermediate Similarity	NPC180183
0.7961	Intermediate Similarity	NPC472896
0.7961	Intermediate Similarity	NPC476538
0.7961	Intermediate Similarity	NPC472897
0.7961	Intermediate Similarity	NPC476539
0.7961	Intermediate Similarity	NPC469984
0.7959	Intermediate Similarity	NPC177818
0.7959	Intermediate Similarity	NPC243728
0.7959	Intermediate Similarity	NPC471770
0.7959	Intermediate Similarity	NPC475032
0.7959	Intermediate Similarity	NPC473890
0.7959	Intermediate Similarity	NPC278939
0.7959	Intermediate Similarity	NPC240372
0.7959	Intermediate Similarity	NPC475033
0.7959	Intermediate Similarity	NPC473555
0.7955	Intermediate Similarity	NPC475
0.7955	Intermediate Similarity	NPC472502
0.7955	Intermediate Similarity	NPC472499
0.7955	Intermediate Similarity	NPC472500
0.7941	Intermediate Similarity	NPC56656
0.7941	Intermediate Similarity	NPC160816
0.7941	Intermediate Similarity	NPC474569
0.7941	Intermediate Similarity	NPC208594
0.7941	Intermediate Similarity	NPC26798
0.7941	Intermediate Similarity	NPC152584
0.7941	Intermediate Similarity	NPC269627
0.7941	Intermediate Similarity	NPC127801
0.7941	Intermediate Similarity	NPC69737
0.7941	Intermediate Similarity	NPC194842
0.7941	Intermediate Similarity	NPC181845
0.7941	Intermediate Similarity	NPC208477
0.7935	Intermediate Similarity	NPC273290
0.7935	Intermediate Similarity	NPC232044
0.7925	Intermediate Similarity	NPC51154
0.7921	Intermediate Similarity	NPC213190
0.7921	Intermediate Similarity	NPC162354
0.7912	Intermediate Similarity	NPC216420
0.7912	Intermediate Similarity	NPC211135
0.7912	Intermediate Similarity	NPC85095
0.7905	Intermediate Similarity	NPC114188
0.7905	Intermediate Similarity	NPC63244
0.7905	Intermediate Similarity	NPC197231
0.7905	Intermediate Similarity	NPC13190
0.7905	Intermediate Similarity	NPC476547
0.7905	Intermediate Similarity	NPC213320
0.79	Intermediate Similarity	NPC176406
0.79	Intermediate Similarity	NPC474022

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 NPC296620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2644
0.2-0.3	4141
0.3-0.4	1374
0.4-0.5	406
0.5-0.6	225
0.6-0.7	92
0.7-0.8	20
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
0.7593	Intermediate Similarity	NPD8133	Approved
0.7568	Intermediate Similarity	NPD7516	Approved
0.7551	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD8377	Approved
0.75	Intermediate Similarity	NPD8294	Approved
0.7477	Intermediate Similarity	NPD7328	Approved
0.7477	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD8335	Approved
0.7434	Intermediate Similarity	NPD8379	Approved
0.7434	Intermediate Similarity	NPD8378	Approved
0.7434	Intermediate Similarity	NPD8033	Approved
0.7434	Intermediate Similarity	NPD8296	Approved
0.7434	Intermediate Similarity	NPD8380	Approved
0.7391	Intermediate Similarity	NPD6928	Phase 2
0.7358	Intermediate Similarity	NPD6412	Phase 2
0.7216	Intermediate Similarity	NPD7524	Approved
0.713	Intermediate Similarity	NPD7503	Approved
0.7034	Intermediate Similarity	NPD7507	Approved
0.7021	Intermediate Similarity	NPD7525	Registered
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7319	Approved
0.6857	Remote Similarity	NPD7638	Approved
0.6852	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6695	Phase 3
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8034	Phase 2
0.6765	Remote Similarity	NPD8035	Phase 2
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.6737	Remote Similarity	NPD7645	Phase 2
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6009	Approved
0.661	Remote Similarity	NPD6319	Approved
0.6607	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4159	Approved
0.6562	Remote Similarity	NPD6929	Approved
0.6559	Remote Similarity	NPD1810	Approved
0.6559	Remote Similarity	NPD1811	Approved
0.6542	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD7750	Discontinued
0.6529	Remote Similarity	NPD7492	Approved
0.6514	Remote Similarity	NPD7632	Discontinued
0.6514	Remote Similarity	NPD5211	Phase 2
0.6504	Remote Similarity	NPD7736	Approved
0.6496	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6930	Phase 2
0.6495	Remote Similarity	NPD6931	Approved
0.6489	Remote Similarity	NPD6942	Approved
0.6489	Remote Similarity	NPD7339	Approved
0.6486	Remote Similarity	NPD6402	Approved
0.6486	Remote Similarity	NPD7128	Approved
0.6486	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD6675	Approved
0.6477	Remote Similarity	NPD371	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6449	Remote Similarity	NPD4755	Approved
0.6446	Remote Similarity	NPD8328	Phase 3
0.6435	Remote Similarity	NPD8297	Approved
0.6435	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD8449	Approved
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6423	Remote Similarity	NPD8293	Discontinued
0.6415	Remote Similarity	NPD7991	Discontinued
0.6404	Remote Similarity	NPD4634	Approved
0.6396	Remote Similarity	NPD5141	Approved
0.6381	Remote Similarity	NPD4202	Approved
0.6378	Remote Similarity	NPD8450	Suspended
0.6372	Remote Similarity	NPD6881	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6354	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD6925	Approved
0.6346	Remote Similarity	NPD3168	Discontinued
0.633	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD5285	Approved
0.633	Remote Similarity	NPD4696	Approved
0.633	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD4748	Discontinued
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6067	Discontinued
0.6289	Remote Similarity	NPD7145	Approved
0.6286	Remote Similarity	NPD7087	Discontinued
0.6281	Remote Similarity	NPD5983	Phase 2
0.6273	Remote Similarity	NPD5344	Discontinued
0.6261	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6933	Approved
0.624	Remote Similarity	NPD6033	Approved
0.6237	Remote Similarity	NPD2686	Approved
0.6237	Remote Similarity	NPD2687	Approved
0.6237	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD2254	Approved
0.6228	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD6399	Phase 3
0.6216	Remote Similarity	NPD5225	Approved
0.6216	Remote Similarity	NPD5226	Approved
0.6216	Remote Similarity	NPD5224	Approved
0.6216	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD6617	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6195	Remote Similarity	NPD6008	Approved
0.6179	Remote Similarity	NPD7604	Phase 2
0.6176	Remote Similarity	NPD7625	Phase 1
0.6176	Remote Similarity	NPD6893	Approved
0.617	Remote Similarity	NPD4243	Approved
0.6162	Remote Similarity	NPD7514	Phase 3
0.6161	Remote Similarity	NPD5175	Approved
0.6161	Remote Similarity	NPD5174	Approved
0.6147	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD6083	Phase 2
0.6139	Remote Similarity	NPD4788	Approved
0.6132	Remote Similarity	NPD7637	Suspended
0.6126	Remote Similarity	NPD5223	Approved
0.6122	Remote Similarity	NPD6697	Approved
0.6122	Remote Similarity	NPD6118	Approved
0.6122	Remote Similarity	NPD6115	Approved
0.6122	Remote Similarity	NPD6114	Approved
0.6117	Remote Similarity	NPD3618	Phase 1
0.61	Remote Similarity	NPD6902	Approved
0.6095	Remote Similarity	NPD5328	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6095	Remote Similarity	NPD6051	Approved
0.608	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6078	Remote Similarity	NPD4786	Approved
0.6068	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4787	Phase 1
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.6042	Remote Similarity	NPD6926	Approved
0.6042	Remote Similarity	NPD6924	Approved
0.6042	Remote Similarity	NPD4785	Approved
0.6042	Remote Similarity	NPD4784	Approved
0.604	Remote Similarity	NPD3667	Approved
0.602	Remote Similarity	NPD6932	Approved
0.602	Remote Similarity	NPD6116	Phase 1
0.6019	Remote Similarity	NPD7748	Approved
0.6018	Remote Similarity	NPD4754	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD6921	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7332	Phase 2
0.5981	Remote Similarity	NPD6079	Approved
0.5981	Remote Similarity	NPD7515	Phase 2
0.598	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3669	Approved
0.5979	Remote Similarity	NPD5275	Approved
0.5979	Remote Similarity	NPD4190	Phase 3
0.5963	Remote Similarity	NPD5695	Phase 3
0.5955	Remote Similarity	NPD1145	Discontinued
0.5948	Remote Similarity	NPD5128	Approved
0.5948	Remote Similarity	NPD4730	Approved
0.5948	Remote Similarity	NPD4729	Approved
0.5946	Remote Similarity	NPD5696	Approved
0.5941	Remote Similarity	NPD6898	Phase 1
0.5932	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6117	Approved
0.5909	Remote Similarity	NPD5221	Approved
0.5909	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4697	Phase 3
0.5909	Remote Similarity	NPD5222	Approved
0.59	Remote Similarity	NPD4195	Approved
0.59	Remote Similarity	NPD6683	Phase 2
0.5893	Remote Similarity	NPD6648	Approved
0.5891	Remote Similarity	NPD5956	Approved
0.5868	Remote Similarity	NPD6940	Discontinued
0.5856	Remote Similarity	NPD5173	Approved
0.5854	Remote Similarity	NPD7100	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