NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	451.31
Volume:	491.543
LogP:	5.523
LogD:	3.986
LogS:	-5.591
# Rotatable Bonds:	4
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	4.861
Fsp3:	0.69
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	1.6662557754898444e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.343
Plasma Protein Binding (PPB):	94.53449249267578%
Volume Distribution (VD):	1.566
Pgp-substrate:	4.4476213455200195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.541
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	4.188
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.836
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.679
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.635
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.837
Carcinogencity:	0.75
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC478140

Natural Product ID:	NPC478140
*Common Name:**	Acetic acid 23beta-hydroxy-14,15,16,17-tetradehydroveratraman-3beta-yl ester
IUPAC Name:	[(3S,6aR,11aS,11bR)-9-[(1S)-1-[(2S,3R,5S)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-3-yl] acetate
Synonyms:
Standard InCHIKey:	JYLXRDJEJNXLAL-NADQLLQKSA-N
Standard InCHI:	InChI=1S/C29H41NO3/c1-16-12-27(32)28(30-15-16)18(3)22-8-9-23-24-7-6-20-13-21(33-19(4)31)10-11-29(20,5)26(24)14-25(23)17(22)2/h6,8-9,16,18,21,24,26-28,30,32H,7,10-15H2,1-5H3/t16-,18-,21-,24-,26-,27+,28-,29-/m0/s1
SMILES:	C[C@H]1C[C@H]([C@@H](NC1)[C@@H](C)C2=C(C3=C(C=C2)[C@@H]4CC=C5C[C@H](CC[C@@]5([C@H]4C3)C)OC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178950
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[25835537]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2219	Cell Line	C2C12	Mus musculus	Activity	=	56	%	PMID[25835537]
NPT2219	Cell Line	C2C12	Mus musculus	Activity	=	24.8	%	PMID[25835537]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4700	nM	PMID[25835537]

☑ 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 NPC478140 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	129
0.1-0.2	731
0.2-0.3	1940
0.3-0.4	8830
0.4-0.5	23469
0.5-0.6	6926
0.6-0.7	653
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC40488
0.745	Intermediate Similarity	NPC473922
0.7261	Intermediate Similarity	NPC93343
0.726	Intermediate Similarity	NPC90693
0.726	Intermediate Similarity	NPC64897
0.7237	Intermediate Similarity	NPC475578
0.7237	Intermediate Similarity	NPC328824
0.72	Intermediate Similarity	NPC57976
0.7192	Intermediate Similarity	NPC313663
0.7179	Intermediate Similarity	NPC275839
0.7154	Intermediate Similarity	NPC56168
0.7152	Intermediate Similarity	NPC217801
0.7143	Intermediate Similarity	NPC132847
0.7132	Intermediate Similarity	NPC176012
0.7092	Intermediate Similarity	NPC291027
0.7092	Intermediate Similarity	NPC213126
0.7092	Intermediate Similarity	NPC169485
0.7092	Intermediate Similarity	NPC317474
0.7092	Intermediate Similarity	NPC84281
0.7087	Intermediate Similarity	NPC474164
0.7059	Intermediate Similarity	NPC311330
0.7032	Intermediate Similarity	NPC476757
0.702	Intermediate Similarity	NPC239770
0.7019	Intermediate Similarity	NPC73644
0.6986	Remote Similarity	NPC69496
0.6959	Remote Similarity	NPC149379
0.6957	Remote Similarity	NPC9274
0.6957	Remote Similarity	NPC235460
0.6943	Remote Similarity	NPC470274
0.694	Remote Similarity	NPC95920
0.694	Remote Similarity	NPC147835
0.694	Remote Similarity	NPC85001
0.694	Remote Similarity	NPC253645
0.6928	Remote Similarity	NPC471516
0.6923	Remote Similarity	NPC94602
0.6892	Remote Similarity	NPC246913
0.6884	Remote Similarity	NPC28280
0.6884	Remote Similarity	NPC304646
0.6866	Remote Similarity	NPC21929
0.6846	Remote Similarity	NPC245836
0.6846	Remote Similarity	NPC233910
0.6828	Remote Similarity	NPC472414
0.6828	Remote Similarity	NPC474847
0.6806	Remote Similarity	NPC472415
0.6805	Remote Similarity	NPC475427
0.6791	Remote Similarity	NPC142326
0.6791	Remote Similarity	NPC94751
0.6781	Remote Similarity	NPC119326
0.6779	Remote Similarity	NPC42423
0.6768	Remote Similarity	NPC476750
0.6767	Remote Similarity	NPC304761
0.6767	Remote Similarity	NPC147000
0.6767	Remote Similarity	NPC150254
0.6767	Remote Similarity	NPC226778
0.6765	Remote Similarity	NPC158854
0.6765	Remote Similarity	NPC24777
0.6765	Remote Similarity	NPC292758
0.6765	Remote Similarity	NPC65855
0.6753	Remote Similarity	NPC108852
0.6753	Remote Similarity	NPC111586
0.6753	Remote Similarity	NPC261709
0.6739	Remote Similarity	NPC478137
0.6731	Remote Similarity	NPC262216
0.6716	Remote Similarity	NPC67043
0.6715	Remote Similarity	NPC79238
0.6714	Remote Similarity	NPC101139
0.671	Remote Similarity	NPC475128
0.671	Remote Similarity	NPC204546
0.6709	Remote Similarity	NPC212799
0.6692	Remote Similarity	NPC324602
0.669	Remote Similarity	NPC182333
0.669	Remote Similarity	NPC314992
0.669	Remote Similarity	NPC273336
0.669	Remote Similarity	NPC35996
0.6689	Remote Similarity	NPC71271
0.6689	Remote Similarity	NPC116057
0.6688	Remote Similarity	NPC44649
0.6687	Remote Similarity	NPC473341
0.6667	Remote Similarity	NPC314192
0.6667	Remote Similarity	NPC242764
0.6667	Remote Similarity	NPC472862
0.6667	Remote Similarity	NPC2265
0.6667	Remote Similarity	NPC105141
0.6644	Remote Similarity	NPC317654
0.6644	Remote Similarity	NPC307020
0.6644	Remote Similarity	NPC96010
0.6644	Remote Similarity	NPC77691
0.6623	Remote Similarity	NPC3202
0.6621	Remote Similarity	NPC109151
0.662	Remote Similarity	NPC45794
0.6618	Remote Similarity	NPC472980
0.6617	Remote Similarity	NPC327226
0.66	Remote Similarity	NPC89769
0.66	Remote Similarity	NPC259665
0.66	Remote Similarity	NPC183722
0.66	Remote Similarity	NPC126859
0.6597	Remote Similarity	NPC477061
0.6597	Remote Similarity	NPC190663
0.6597	Remote Similarity	NPC478138
0.6597	Remote Similarity	NPC45777
0.6594	Remote Similarity	NPC474459
0.6593	Remote Similarity	NPC471186
0.6582	Remote Similarity	NPC237240
0.6582	Remote Similarity	NPC31171
0.6582	Remote Similarity	NPC260194
0.6579	Remote Similarity	NPC159811
0.6577	Remote Similarity	NPC472413
0.6577	Remote Similarity	NPC66177
0.6577	Remote Similarity	NPC268763
0.6577	Remote Similarity	NPC8305
0.6575	Remote Similarity	NPC478058
0.6573	Remote Similarity	NPC254233
0.6569	Remote Similarity	NPC475006
0.6562	Remote Similarity	NPC220596
0.6554	Remote Similarity	NPC65310
0.6554	Remote Similarity	NPC278097
0.6549	Remote Similarity	NPC470820
0.6547	Remote Similarity	NPC474452
0.6547	Remote Similarity	NPC471189
0.6545	Remote Similarity	NPC471527
0.6544	Remote Similarity	NPC85560
0.6544	Remote Similarity	NPC244933
0.6541	Remote Similarity	NPC473541
0.6541	Remote Similarity	NPC133809
0.6541	Remote Similarity	NPC264728
0.6541	Remote Similarity	NPC136810
0.6541	Remote Similarity	NPC225079
0.6541	Remote Similarity	NPC128248
0.6538	Remote Similarity	NPC161069
0.6536	Remote Similarity	NPC203486
0.6533	Remote Similarity	NPC124802
0.6532	Remote Similarity	NPC203005
0.6531	Remote Similarity	NPC307139
0.6522	Remote Similarity	NPC472313
0.6519	Remote Similarity	NPC212874
0.6519	Remote Similarity	NPC472103
0.6516	Remote Similarity	NPC239762
0.6516	Remote Similarity	NPC163392
0.6516	Remote Similarity	NPC262324
0.6516	Remote Similarity	NPC153007
0.6516	Remote Similarity	NPC243893
0.6515	Remote Similarity	NPC120393
0.651	Remote Similarity	NPC5486
0.6507	Remote Similarity	NPC296686
0.6507	Remote Similarity	NPC160493
0.6496	Remote Similarity	NPC472979
0.6496	Remote Similarity	NPC159367
0.6496	Remote Similarity	NPC27252
0.6494	Remote Similarity	NPC208725
0.6494	Remote Similarity	NPC471864
0.649	Remote Similarity	NPC475138
0.6489	Remote Similarity	NPC289140
0.6483	Remote Similarity	NPC133389
0.6483	Remote Similarity	NPC234337
0.6483	Remote Similarity	NPC183339
0.6475	Remote Similarity	NPC133308
0.6474	Remote Similarity	NPC150712
0.6471	Remote Similarity	NPC243601
0.6471	Remote Similarity	NPC233256
0.6471	Remote Similarity	NPC228511
0.6471	Remote Similarity	NPC195841
0.6471	Remote Similarity	NPC476749
0.6467	Remote Similarity	NPC295478
0.6466	Remote Similarity	NPC221825
0.6463	Remote Similarity	NPC12016
0.646	Remote Similarity	NPC201692
0.6458	Remote Similarity	NPC310467
0.6454	Remote Similarity	NPC169616
0.6452	Remote Similarity	NPC77992
0.6449	Remote Similarity	NPC64642
0.6449	Remote Similarity	NPC472982
0.6449	Remote Similarity	NPC149455
0.6447	Remote Similarity	NPC246079
0.6444	Remote Similarity	NPC19856
0.6443	Remote Similarity	NPC477937
0.6439	Remote Similarity	NPC226041
0.6439	Remote Similarity	NPC469891
0.6439	Remote Similarity	NPC469892
0.6439	Remote Similarity	NPC469890
0.6438	Remote Similarity	NPC173934
0.6438	Remote Similarity	NPC264589
0.6438	Remote Similarity	NPC71684
0.6434	Remote Similarity	NPC212891
0.6433	Remote Similarity	NPC79921
0.6429	Remote Similarity	NPC471188
0.6429	Remote Similarity	NPC279045
0.6429	Remote Similarity	NPC113325
0.6424	Remote Similarity	NPC477156
0.6424	Remote Similarity	NPC477157
0.6423	Remote Similarity	NPC327481
0.6419	Remote Similarity	NPC472373
0.6419	Remote Similarity	NPC328107
0.6419	Remote Similarity	NPC470815
0.6418	Remote Similarity	NPC214200
0.6418	Remote Similarity	NPC474582
0.6418	Remote Similarity	NPC469481
0.6418	Remote Similarity	NPC228400
0.6415	Remote Similarity	NPC49565
0.6414	Remote Similarity	NPC202015
0.6412	Remote Similarity	NPC469462

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 NPC478140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	427
0.2-0.3	820
0.3-0.4	2131
0.4-0.5	3419
0.5-0.6	1832
0.6-0.7	415
0.7-0.8	14
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
0.782	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1710	Approved
0.7353	Intermediate Similarity	NPD7522	Discontinued
0.7338	Intermediate Similarity	NPD5618	Discontinued
0.7319	Intermediate Similarity	NPD4416	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5705	Approved
0.7308	Intermediate Similarity	NPD5704	Approved
0.7308	Intermediate Similarity	NPD5706	Approved
0.726	Intermediate Similarity	NPD6623	Phase 3
0.7237	Intermediate Similarity	NPD8131	Suspended
0.7219	Intermediate Similarity	NPD3638	Discontinued
0.7206	Intermediate Similarity	NPD4031	Approved
0.7206	Intermediate Similarity	NPD4032	Approved
0.7206	Intermediate Similarity	NPD7508	Discontinued
0.7194	Intermediate Similarity	NPD7725	Approved
0.7192	Intermediate Similarity	NPD7715	Approved
0.7192	Intermediate Similarity	NPD7714	Approved
0.7174	Intermediate Similarity	NPD2106	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7488	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4574	Approved
0.7153	Intermediate Similarity	NPD4576	Approved
0.7114	Intermediate Similarity	NPD6294	Approved
0.7114	Intermediate Similarity	NPD6295	Approved
0.7113	Intermediate Similarity	NPD6025	Phase 1
0.7092	Intermediate Similarity	NPD3132	Approved
0.7092	Intermediate Similarity	NPD2612	Approved
0.7092	Intermediate Similarity	NPD2608	Approved
0.7092	Intermediate Similarity	NPD2611	Approved
0.7092	Intermediate Similarity	NPD2609	Approved
0.7092	Intermediate Similarity	NPD4218	Approved
0.7092	Intermediate Similarity	NPD4215	Approved
0.7092	Intermediate Similarity	NPD4216	Approved
0.7092	Intermediate Similarity	NPD4217	Approved
0.7092	Intermediate Similarity	NPD3131	Approved
0.7092	Intermediate Similarity	NPD2610	Approved
0.7091	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1371	Approved
0.7059	Intermediate Similarity	NPD1370	Approved
0.7059	Intermediate Similarity	NPD1373	Approved
0.7059	Intermediate Similarity	NPD1374	Approved
0.705	Intermediate Similarity	NPD5511	Discontinued
0.705	Intermediate Similarity	NPD4479	Discontinued
0.7	Intermediate Similarity	NPD4719	Phase 2
0.6986	Remote Similarity	NPD2613	Approved
0.6978	Remote Similarity	NPD6065	Approved
0.6974	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5162	Approved
0.6901	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4813	Approved
0.6899	Remote Similarity	NPD4727	Phase 1
0.6899	Remote Similarity	NPD4263	Approved
0.6892	Remote Similarity	NPD5581	Approved
0.689	Remote Similarity	NPD5709	Phase 3
0.6884	Remote Similarity	NPD4766	Approved
0.6879	Remote Similarity	NPD3645	Discontinued
0.6875	Remote Similarity	NPD4677	Discontinued
0.6848	Remote Similarity	NPD4666	Phase 3
0.6846	Remote Similarity	NPD3614	Approved
0.6846	Remote Similarity	NPD4745	Approved
0.6846	Remote Similarity	NPD2570	Approved
0.6846	Remote Similarity	NPD3087	Approved
0.6846	Remote Similarity	NPD3090	Approved
0.6846	Remote Similarity	NPD3088	Approved
0.6846	Remote Similarity	NPD2566	Approved
0.6846	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2573	Approved
0.6846	Remote Similarity	NPD3615	Approved
0.6846	Remote Similarity	NPD2574	Discontinued
0.6846	Remote Similarity	NPD3089	Approved
0.6846	Remote Similarity	NPD3616	Approved
0.6846	Remote Similarity	NPD2571	Approved
0.6846	Remote Similarity	NPD4746	Phase 3
0.6813	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5120	Approved
0.68	Remote Similarity	NPD5121	Approved
0.68	Remote Similarity	NPD5119	Approved
0.6786	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3826	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6852	Discontinued
0.6767	Remote Similarity	NPD310	Approved
0.6767	Remote Similarity	NPD315	Approved
0.6767	Remote Similarity	NPD311	Approved
0.6767	Remote Similarity	NPD309	Approved
0.6767	Remote Similarity	NPD10	Approved
0.6767	Remote Similarity	NPD314	Approved
0.6765	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1756	Approved
0.6765	Remote Similarity	NPD551	Approved
0.6765	Remote Similarity	NPD550	Approved
0.6765	Remote Similarity	NPD1752	Approved
0.6761	Remote Similarity	NPD1922	Discontinued
0.6757	Remote Similarity	NPD4617	Approved
0.6757	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4620	Approved
0.6757	Remote Similarity	NPD5203	Approved
0.6757	Remote Similarity	NPD5201	Approved
0.6755	Remote Similarity	NPD4686	Approved
0.6755	Remote Similarity	NPD4685	Phase 3
0.6755	Remote Similarity	NPD4684	Phase 3
0.6741	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2607	Approved
0.6739	Remote Similarity	NPD7094	Approved
0.6739	Remote Similarity	NPD6858	Approved
0.6736	Remote Similarity	NPD7437	Approved
0.6736	Remote Similarity	NPD7436	Approved
0.6733	Remote Similarity	NPD6405	Approved
0.6733	Remote Similarity	NPD6407	Approved
0.6733	Remote Similarity	NPD8118	Discontinued
0.6732	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6677	Suspended
0.6716	Remote Similarity	NPD5717	Approved
0.6713	Remote Similarity	NPD7342	Discontinued
0.6711	Remote Similarity	NPD6073	Approved
0.6706	Remote Similarity	NPD6620	Discovery
0.669	Remote Similarity	NPD7250	Approved
0.669	Remote Similarity	NPD7249	Approved
0.669	Remote Similarity	NPD2562	Approved
0.669	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2217	Approved
0.669	Remote Similarity	NPD2561	Approved
0.669	Remote Similarity	NPD7814	Approved
0.669	Remote Similarity	NPD2218	Phase 2
0.6687	Remote Similarity	NPD6315	Phase 2
0.6667	Remote Similarity	NPD6564	Approved
0.6667	Remote Similarity	NPD6563	Approved
0.6667	Remote Similarity	NPD5576	Approved
0.6667	Remote Similarity	NPD6565	Approved
0.6667	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5579	Approved
0.6646	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7430	Approved
0.6645	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7431	Approved
0.6644	Remote Similarity	NPD2606	Approved
0.6644	Remote Similarity	NPD4659	Approved
0.6644	Remote Similarity	NPD2605	Approved
0.6643	Remote Similarity	NPD770	Discontinued
0.6643	Remote Similarity	NPD5981	Approved
0.6625	Remote Similarity	NPD6222	Approved
0.6625	Remote Similarity	NPD6221	Approved
0.6624	Remote Similarity	NPD6676	Phase 2
0.6621	Remote Similarity	NPD3381	Discontinued
0.6621	Remote Similarity	NPD3529	Phase 2
0.6621	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8165	Discontinued
0.6601	Remote Similarity	NPD5725	Approved
0.6601	Remote Similarity	NPD6544	Discontinued
0.6601	Remote Similarity	NPD8125	Discontinued
0.66	Remote Similarity	NPD5155	Approved
0.66	Remote Similarity	NPD5156	Approved
0.6599	Remote Similarity	NPD2198	Approved
0.6599	Remote Similarity	NPD2199	Approved
0.6594	Remote Similarity	NPD3643	Approved
0.6594	Remote Similarity	NPD4253	Approved
0.6594	Remote Similarity	NPD3642	Approved
0.6594	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3644	Approved
0.6594	Remote Similarity	NPD4254	Approved
0.6589	Remote Similarity	NPD3718	Approved
0.6589	Remote Similarity	NPD3719	Approved
0.6582	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5182	Approved
0.6579	Remote Similarity	NPD3373	Approved
0.6579	Remote Similarity	NPD5185	Approved
0.6579	Remote Similarity	NPD5296	Approved
0.6579	Remote Similarity	NPD5184	Approved
0.6577	Remote Similarity	NPD4175	Approved
0.6577	Remote Similarity	NPD3635	Approved
0.6577	Remote Similarity	NPD3637	Approved
0.6577	Remote Similarity	NPD4177	Approved
0.6577	Remote Similarity	NPD3636	Approved
0.6571	Remote Similarity	NPD2650	Approved
0.6571	Remote Similarity	NPD2652	Approved
0.6565	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2627	Approved
0.6554	Remote Similarity	NPD2159	Approved
0.6554	Remote Similarity	NPD2628	Approved
0.6554	Remote Similarity	NPD2626	Approved
0.6554	Remote Similarity	NPD4103	Phase 2
0.6554	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2625	Approved
0.6554	Remote Similarity	NPD2160	Approved
0.6552	Remote Similarity	NPD3881	Discontinued
0.6552	Remote Similarity	NPD7813	Approved
0.6552	Remote Similarity	NPD7815	Approved
0.6543	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4726	Approved
0.6538	Remote Similarity	NPD4721	Approved
0.6538	Remote Similarity	NPD4725	Approved
0.6533	Remote Similarity	NPD3594	Approved
0.6533	Remote Similarity	NPD3595	Approved
0.6533	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6993	Approved
0.6528	Remote Similarity	NPD6994	Approved
0.6527	Remote Similarity	NPD6635	Approved
0.6525	Remote Similarity	NPD747	Discontinued

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