NPASS Compound

Structure

NPC472984 OpenBabel07101718292D 22 23 0 0 1 0 0 0 0 0999 V2000 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 2.5981 -1.5000 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 -5.0000 0.0000 C 0 0 0 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 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 -0.8660 -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 0 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 19 1 1 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 16 18 1 0 0 0 0 16 19 1 1 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 19 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.24
Volume:	341.165
LogP:	2.742
LogD:	2.65
LogS:	-1.791
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.86
Synthetic Accessibility Score:	4.14
Fsp3:	0.895
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:	-4.763
MDCK Permeability:	1.623654316063039e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.782
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.896
Plasma Protein Binding (PPB):	69.97197723388672%
Volume Distribution (VD):	0.869
Pgp-substrate:	21.97210121154785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.247
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.475
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.651
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	9.462
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.568
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.299
Carcinogencity:	0.076
Eye Corrosion:	0.151
Eye Irritation:	0.278
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472984

Natural Product ID:	NPC472984
*Common Name:**	QVIBGLUOQYVZRY-QUIPCFFLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QVIBGLUOQYVZRY-QUIPCFFLSA-N
Standard InCHI:	InChI=1S/C19H32O3/c1-12(2)15(21)7-6-13-10-14(20)11-16-18(3,4)17(22)8-9-19(13,16)5/h12-13,16-17,22H,6-11H2,1-5H3/t13-,16-,17-,19+/m1/s1
SMILES:	O=C1C[C@@H](CCC(=O)C(C)C)[C@]2([C@H](C1)C(C)(C)[C@@H](CC2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594348
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32900	chloranthus sessilifolius	Species	Chloranthaceae	Eukaryota	Whole plants	Fengqi Mountains, Sichuan Province, China	2012-Aug	PMID[26126961]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[450332]

☑ 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 NPC472984 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	348
0.1-0.2	3089
0.2-0.3	11541
0.3-0.4	13541
0.4-0.5	6518
0.5-0.6	4982
0.6-0.7	2359
0.7-0.8	291
0.8-0.85	27
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8857	High Similarity	NPC472487
0.8857	High Similarity	NPC472486
0.8732	High Similarity	NPC221420
0.8714	High Similarity	NPC159789
0.8714	High Similarity	NPC125767
0.8714	High Similarity	NPC21220
0.8696	High Similarity	NPC68426
0.8696	High Similarity	NPC232112
0.8696	High Similarity	NPC477229
0.8696	High Similarity	NPC282905
0.8592	High Similarity	NPC5767
0.8592	High Similarity	NPC475742
0.8571	High Similarity	NPC159325
0.8571	High Similarity	NPC133922
0.8571	High Similarity	NPC168511
0.8551	High Similarity	NPC320549
0.8551	High Similarity	NPC58057
0.8551	High Similarity	NPC89310
0.8551	High Similarity	NPC151018
0.8551	High Similarity	NPC156277
0.8529	High Similarity	NPC327728
0.8529	High Similarity	NPC213178
0.8529	High Similarity	NPC6120
0.8529	High Similarity	NPC131892
0.8493	Intermediate Similarity	NPC320144
0.8451	Intermediate Similarity	NPC195155
0.8451	Intermediate Similarity	NPC267753
0.8451	Intermediate Similarity	NPC97534
0.8451	Intermediate Similarity	NPC273366
0.8451	Intermediate Similarity	NPC174964
0.8429	Intermediate Similarity	NPC81759
0.8382	Intermediate Similarity	NPC474954
0.8356	Intermediate Similarity	NPC185465
0.8333	Intermediate Similarity	NPC108840
0.831	Intermediate Similarity	NPC254340
0.831	Intermediate Similarity	NPC130011
0.8235	Intermediate Similarity	NPC41542
0.8219	Intermediate Similarity	NPC475031
0.8219	Intermediate Similarity	NPC23884
0.8219	Intermediate Similarity	NPC472746
0.8209	Intermediate Similarity	NPC19311
0.8209	Intermediate Similarity	NPC230047
0.8194	Intermediate Similarity	NPC212733
0.8133	Intermediate Similarity	NPC164999
0.8116	Intermediate Similarity	NPC260319
0.8116	Intermediate Similarity	NPC2568
0.8116	Intermediate Similarity	NPC180777
0.8116	Intermediate Similarity	NPC103647
0.8108	Intermediate Similarity	NPC475725
0.8082	Intermediate Similarity	NPC4209
0.8056	Intermediate Similarity	NPC167702
0.8056	Intermediate Similarity	NPC280026
0.8052	Intermediate Similarity	NPC327451
0.8026	Intermediate Similarity	NPC476071
0.8	Intermediate Similarity	NPC321732
0.8	Intermediate Similarity	NPC324607
0.8	Intermediate Similarity	NPC275243
0.7973	Intermediate Similarity	NPC317913
0.7973	Intermediate Similarity	NPC143133
0.7973	Intermediate Similarity	NPC298168
0.7973	Intermediate Similarity	NPC207010
0.7969	Intermediate Similarity	NPC135438
0.7949	Intermediate Similarity	NPC237938
0.7949	Intermediate Similarity	NPC477434
0.7949	Intermediate Similarity	NPC50438
0.7949	Intermediate Similarity	NPC219535
0.7922	Intermediate Similarity	NPC61107
0.7922	Intermediate Similarity	NPC317066
0.7922	Intermediate Similarity	NPC30583
0.7922	Intermediate Similarity	NPC289486
0.7922	Intermediate Similarity	NPC268040
0.7917	Intermediate Similarity	NPC310766
0.7895	Intermediate Similarity	NPC477851
0.7867	Intermediate Similarity	NPC472608
0.7867	Intermediate Similarity	NPC478084
0.7867	Intermediate Similarity	NPC224802
0.7867	Intermediate Similarity	NPC34046
0.7867	Intermediate Similarity	NPC171426
0.7867	Intermediate Similarity	NPC80089
0.7867	Intermediate Similarity	NPC324700
0.7867	Intermediate Similarity	NPC26029
0.7857	Intermediate Similarity	NPC478228
0.7838	Intermediate Similarity	NPC474020
0.7792	Intermediate Similarity	NPC50658
0.7792	Intermediate Similarity	NPC469745
0.7778	Intermediate Similarity	NPC247195
0.7778	Intermediate Similarity	NPC290058
0.7763	Intermediate Similarity	NPC201276
0.7763	Intermediate Similarity	NPC80891
0.775	Intermediate Similarity	NPC80700
0.775	Intermediate Similarity	NPC475276
0.775	Intermediate Similarity	NPC476726
0.775	Intermediate Similarity	NPC83242
0.775	Intermediate Similarity	NPC476727
0.7733	Intermediate Similarity	NPC474433
0.7722	Intermediate Similarity	NPC146683
0.7722	Intermediate Similarity	NPC105895
0.7714	Intermediate Similarity	NPC328304
0.7714	Intermediate Similarity	NPC329466
0.7703	Intermediate Similarity	NPC179858
0.7692	Intermediate Similarity	NPC48362
0.7692	Intermediate Similarity	NPC236588
0.7681	Intermediate Similarity	NPC469791
0.7662	Intermediate Similarity	NPC470609
0.7654	Intermediate Similarity	NPC57469
0.7654	Intermediate Similarity	NPC263802
0.7654	Intermediate Similarity	NPC4643
0.7639	Intermediate Similarity	NPC476731
0.7632	Intermediate Similarity	NPC31031
0.7632	Intermediate Similarity	NPC243594
0.7625	Intermediate Similarity	NPC62572
0.7625	Intermediate Similarity	NPC473350
0.7606	Intermediate Similarity	NPC475977
0.76	Intermediate Similarity	NPC471046
0.7595	Intermediate Similarity	NPC163616
0.7595	Intermediate Similarity	NPC475726
0.7595	Intermediate Similarity	NPC118800
0.7595	Intermediate Similarity	NPC227170
0.7595	Intermediate Similarity	NPC472743
0.7568	Intermediate Similarity	NPC472854
0.7568	Intermediate Similarity	NPC162164
0.7564	Intermediate Similarity	NPC58631
0.7564	Intermediate Similarity	NPC48756
0.7564	Intermediate Similarity	NPC12933
0.7564	Intermediate Similarity	NPC280781
0.7564	Intermediate Similarity	NPC328264
0.7561	Intermediate Similarity	NPC3032
0.7561	Intermediate Similarity	NPC477614
0.7561	Intermediate Similarity	NPC226491
0.7561	Intermediate Similarity	NPC473319
0.7561	Intermediate Similarity	NPC131104
0.7534	Intermediate Similarity	NPC126642
0.7534	Intermediate Similarity	NPC473267
0.7534	Intermediate Similarity	NPC478227
0.7532	Intermediate Similarity	NPC472310
0.7531	Intermediate Similarity	NPC472272
0.7531	Intermediate Similarity	NPC248216
0.7531	Intermediate Similarity	NPC34190
0.7531	Intermediate Similarity	NPC120395
0.7531	Intermediate Similarity	NPC302111
0.75	Intermediate Similarity	NPC473336
0.75	Intermediate Similarity	NPC112463
0.75	Intermediate Similarity	NPC149249
0.75	Intermediate Similarity	NPC475745
0.75	Intermediate Similarity	NPC474996
0.75	Intermediate Similarity	NPC25037
0.75	Intermediate Similarity	NPC474482
0.75	Intermediate Similarity	NPC252032
0.75	Intermediate Similarity	NPC471044
0.75	Intermediate Similarity	NPC264602
0.75	Intermediate Similarity	NPC469941
0.75	Intermediate Similarity	NPC34984
0.75	Intermediate Similarity	NPC475689
0.75	Intermediate Similarity	NPC476734
0.75	Intermediate Similarity	NPC319671
0.75	Intermediate Similarity	NPC307865
0.747	Intermediate Similarity	NPC67653
0.747	Intermediate Similarity	NPC61688
0.747	Intermediate Similarity	NPC69627
0.747	Intermediate Similarity	NPC477443
0.747	Intermediate Similarity	NPC471459
0.747	Intermediate Similarity	NPC477440
0.747	Intermediate Similarity	NPC472973
0.7468	Intermediate Similarity	NPC328007
0.7468	Intermediate Similarity	NPC121121
0.7467	Intermediate Similarity	NPC472311
0.7465	Intermediate Similarity	NPC476928
0.7439	Intermediate Similarity	NPC470920
0.7439	Intermediate Similarity	NPC472495
0.7439	Intermediate Similarity	NPC174619
0.7439	Intermediate Similarity	NPC153604
0.7439	Intermediate Similarity	NPC298904
0.7439	Intermediate Similarity	NPC472497
0.7436	Intermediate Similarity	NPC261616
0.7429	Intermediate Similarity	NPC260116
0.7429	Intermediate Similarity	NPC80463
0.7407	Intermediate Similarity	NPC470574
0.7407	Intermediate Similarity	NPC477205
0.7407	Intermediate Similarity	NPC292553
0.7407	Intermediate Similarity	NPC133954
0.7407	Intermediate Similarity	NPC76518
0.7407	Intermediate Similarity	NPC477445
0.7407	Intermediate Similarity	NPC197823
0.7403	Intermediate Similarity	NPC329117
0.7397	Intermediate Similarity	NPC91369
0.7397	Intermediate Similarity	NPC477929
0.7391	Intermediate Similarity	NPC292419
0.7391	Intermediate Similarity	NPC114891
0.7391	Intermediate Similarity	NPC290791
0.7385	Intermediate Similarity	NPC471269
0.7381	Intermediate Similarity	NPC477433
0.7381	Intermediate Similarity	NPC477442
0.7381	Intermediate Similarity	NPC475211
0.7381	Intermediate Similarity	NPC476296
0.7381	Intermediate Similarity	NPC477444
0.7381	Intermediate Similarity	NPC88337
0.7375	Intermediate Similarity	NPC15091
0.7375	Intermediate Similarity	NPC64600
0.7375	Intermediate Similarity	NPC269684
0.7375	Intermediate Similarity	NPC471036

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 NPC472984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	3627
0.2-0.3	3404
0.3-0.4	1062
0.4-0.5	289
0.5-0.6	236
0.6-0.7	77
0.7-0.8	19
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8714	High Similarity	NPD3703	Phase 2
0.8551	High Similarity	NPD4808	Clinical (unspecified phase)
0.8551	High Similarity	NPD4809	Clinical (unspecified phase)
0.8529	High Similarity	NPD3700	Clinical (unspecified phase)
0.8529	High Similarity	NPD3699	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD4245	Approved
0.8143	Intermediate Similarity	NPD4244	Approved
0.8082	Intermediate Similarity	NPD6117	Approved
0.8056	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3698	Phase 2
0.7973	Intermediate Similarity	NPD6116	Phase 1
0.7887	Intermediate Similarity	NPD4789	Approved
0.7867	Intermediate Similarity	NPD6115	Approved
0.7867	Intermediate Similarity	NPD6114	Approved
0.7867	Intermediate Similarity	NPD6697	Approved
0.7867	Intermediate Similarity	NPD6118	Approved
0.7857	Intermediate Similarity	NPD5360	Phase 3
0.7857	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3671	Phase 1
0.747	Intermediate Similarity	NPD5328	Approved
0.7324	Intermediate Similarity	NPD4224	Phase 2
0.7297	Intermediate Similarity	NPD4758	Discontinued
0.7294	Intermediate Similarity	NPD6079	Approved
0.7195	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3618	Phase 1
0.7073	Intermediate Similarity	NPD4786	Approved
0.7067	Intermediate Similarity	NPD5777	Approved
0.7067	Intermediate Similarity	NPD6081	Approved
0.7037	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3702	Approved
0.697	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5364	Discontinued
0.6897	Remote Similarity	NPD7515	Phase 2
0.6778	Remote Similarity	NPD4697	Phase 3
0.6778	Remote Similarity	NPD5222	Approved
0.6778	Remote Similarity	NPD5221	Approved
0.6778	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4788	Approved
0.6714	Remote Similarity	NPD3198	Approved
0.6711	Remote Similarity	NPD4787	Phase 1
0.6703	Remote Similarity	NPD4755	Approved
0.6703	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD384	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD385	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6629	Remote Similarity	NPD4202	Approved
0.6575	Remote Similarity	NPD7909	Approved
0.6559	Remote Similarity	NPD4700	Approved
0.6559	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5285	Approved
0.6559	Remote Similarity	NPD5286	Approved
0.6556	Remote Similarity	NPD7748	Approved
0.6517	Remote Similarity	NPD8035	Phase 2
0.6517	Remote Similarity	NPD8034	Phase 2
0.6489	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5226	Approved
0.6421	Remote Similarity	NPD5211	Phase 2
0.6421	Remote Similarity	NPD4633	Approved
0.6421	Remote Similarity	NPD5224	Approved
0.6421	Remote Similarity	NPD5225	Approved
0.6392	Remote Similarity	NPD6402	Approved
0.6392	Remote Similarity	NPD5739	Approved
0.6392	Remote Similarity	NPD6675	Approved
0.6392	Remote Similarity	NPD7128	Approved
0.6354	Remote Similarity	NPD4754	Approved
0.6354	Remote Similarity	NPD5175	Approved
0.6354	Remote Similarity	NPD5174	Approved
0.6344	Remote Similarity	NPD7902	Approved
0.6341	Remote Similarity	NPD3617	Approved
0.6322	Remote Similarity	NPD5279	Phase 3
0.6289	Remote Similarity	NPD5141	Approved
0.6289	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3668	Phase 3
0.6267	Remote Similarity	NPD7341	Phase 2
0.6265	Remote Similarity	NPD7645	Phase 2
0.6264	Remote Similarity	NPD6399	Phase 3
0.6263	Remote Similarity	NPD7320	Approved
0.6263	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6881	Approved
0.6263	Remote Similarity	NPD6899	Approved
0.6224	Remote Similarity	NPD4767	Approved
0.6224	Remote Similarity	NPD4768	Approved
0.6211	Remote Similarity	NPD8418	Phase 2
0.62	Remote Similarity	NPD6373	Approved
0.62	Remote Similarity	NPD6372	Approved
0.619	Remote Similarity	NPD4695	Discontinued
0.619	Remote Similarity	NPD7525	Registered
0.6162	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD7290	Approved
0.6139	Remote Similarity	NPD6883	Approved
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4753	Phase 2
0.61	Remote Similarity	NPD5168	Approved
0.61	Remote Similarity	NPD6011	Approved
0.61	Remote Similarity	NPD4730	Approved
0.61	Remote Similarity	NPD5128	Approved
0.61	Remote Similarity	NPD4729	Approved
0.6078	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6649	Approved
0.6078	Remote Similarity	NPD6869	Approved
0.6078	Remote Similarity	NPD6847	Approved
0.6078	Remote Similarity	NPD6617	Approved
0.6078	Remote Similarity	NPD6650	Approved
0.6078	Remote Similarity	NPD8130	Phase 1
0.6067	Remote Similarity	NPD3573	Approved
0.6047	Remote Similarity	NPD4221	Approved
0.6047	Remote Similarity	NPD4223	Phase 3
0.604	Remote Similarity	NPD6014	Approved
0.604	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD6013	Approved
0.6026	Remote Similarity	NPD6705	Phase 1
0.6023	Remote Similarity	NPD5329	Approved
0.6022	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7900	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD634	Phase 3
0.598	Remote Similarity	NPD5250	Approved
0.598	Remote Similarity	NPD5251	Approved
0.598	Remote Similarity	NPD5247	Approved
0.598	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5135	Approved
0.598	Remote Similarity	NPD5169	Approved
0.598	Remote Similarity	NPD5248	Approved
0.598	Remote Similarity	NPD5249	Phase 3
0.598	Remote Similarity	NPD4634	Approved
0.5976	Remote Similarity	NPD6942	Approved
0.5976	Remote Similarity	NPD7339	Approved
0.5955	Remote Similarity	NPD6409	Approved
0.5955	Remote Similarity	NPD7334	Approved
0.5955	Remote Similarity	NPD7521	Approved
0.5955	Remote Similarity	NPD7146	Approved
0.5955	Remote Similarity	NPD5330	Approved
0.5955	Remote Similarity	NPD6684	Approved
0.5949	Remote Similarity	NPD3726	Approved
0.5949	Remote Similarity	NPD3725	Approved
0.5942	Remote Similarity	NPD3186	Phase 1
0.5938	Remote Similarity	NPD7638	Approved
0.5934	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6101	Approved
0.593	Remote Similarity	NPD4692	Approved
0.593	Remote Similarity	NPD4139	Approved
0.5922	Remote Similarity	NPD5217	Approved
0.5922	Remote Similarity	NPD5216	Approved
0.5922	Remote Similarity	NPD5215	Approved
0.5922	Remote Similarity	NPD5127	Approved
0.5921	Remote Similarity	NPD371	Approved
0.5909	Remote Similarity	NPD4197	Approved
0.5904	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6920	Discontinued
0.5882	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD7640	Approved
0.5854	Remote Similarity	NPD6926	Approved
0.5854	Remote Similarity	NPD6924	Approved
0.5849	Remote Similarity	NPD6868	Approved
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5824	Remote Similarity	NPD6903	Approved
0.5824	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5368	Approved
0.581	Remote Similarity	NPD4632	Approved
0.5789	Remote Similarity	NPD4629	Approved
0.5789	Remote Similarity	NPD5210	Approved
0.5784	Remote Similarity	NPD6415	Discontinued
0.5778	Remote Similarity	NPD4138	Approved
0.5778	Remote Similarity	NPD4689	Approved
0.5778	Remote Similarity	NPD4693	Phase 3
0.5778	Remote Similarity	NPD4688	Approved
0.5778	Remote Similarity	NPD4519	Discontinued
0.5778	Remote Similarity	NPD4623	Approved
0.5778	Remote Similarity	NPD5205	Approved
0.5778	Remote Similarity	NPD4690	Approved
0.5769	Remote Similarity	NPD7331	Phase 2
0.5765	Remote Similarity	NPD4802	Phase 2
0.5765	Remote Similarity	NPD4238	Approved
0.5765	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD386	Approved
0.5758	Remote Similarity	NPD7632	Discontinued
0.5758	Remote Similarity	NPD388	Approved
0.5755	Remote Similarity	NPD5167	Approved
0.5745	Remote Similarity	NPD5779	Approved
0.5745	Remote Similarity	NPD5778	Approved
0.5741	Remote Similarity	NPD6335	Approved
0.5714	Remote Similarity	NPD6933	Approved
0.5701	Remote Similarity	NPD6274	Approved
0.5688	Remote Similarity	NPD7100	Approved
0.5688	Remote Similarity	NPD7101	Approved
0.5682	Remote Similarity	NPD6435	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