NPASS Compound

Structure

NPC474962 OpenBabel07101718292D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8536 5.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2137 4.0428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.488
LogD:	5.079
LogS:	-4.962
# Rotatable Bonds:	6
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.384
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.373
MDCK Permeability:	1.405429338774411e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	96.14867401123047%
Volume Distribution (VD):	1.112
Pgp-substrate:	1.8899980783462524%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	4.033
Half-life (T1/2):	0.36

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.419
Skin Sensitization:	0.854
Carcinogencity:	0.294
Eye Corrosion:	0.033
Eye Irritation:	0.175
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC474962

Natural Product ID:	NPC474962
*Common Name:**	Dihydroschizandronic Acid
IUPAC Name:	n.a.
Synonyms:	Dihydroschizandronic Acid
Standard InCHIKey:	IIUXRYBFJIQPEV-KABYOLABSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(8-7-9-20(2)25(32)33)21-12-14-28(6)23-11-10-22-26(3,4)24(31)13-15-29(22)18-30(23,29)17-16-27(21,28)5/h19-23H,7-18H2,1-6H3,(H,32,33)/t19-,20?,21-,22+,23+,27-,28+,29-,30+/m1/s1
SMILES:	CC(CCCC(C)C(=O)O)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(=O)C5(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490332
PubChem CID:	21626062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	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
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	43900.0	nM	PMID[534732]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	43900.0	nM	PMID[534732]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	0.0	%	PMID[534732]

☑ 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 NPC474962 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	300
0.1-0.2	4127
0.2-0.3	17542
0.3-0.4	7471
0.4-0.5	6644
0.5-0.6	4620
0.6-0.7	1607
0.7-0.8	291
0.8-0.85	67
0.85-0.9	20
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC474221
0.9385	High Similarity	NPC130459
0.9385	High Similarity	NPC478180
0.9254	High Similarity	NPC108131
0.9231	High Similarity	NPC42060
0.8971	High Similarity	NPC477850
0.8939	High Similarity	NPC477931
0.8939	High Similarity	NPC268736
0.8824	High Similarity	NPC196197
0.8824	High Similarity	NPC252032
0.8824	High Similarity	NPC476734
0.8824	High Similarity	NPC469941
0.8824	High Similarity	NPC319671
0.8696	High Similarity	NPC477929
0.8676	High Similarity	NPC473225
0.8592	High Similarity	NPC167702
0.8592	High Similarity	NPC280026
0.8571	High Similarity	NPC472309
0.8571	High Similarity	NPC473267
0.8571	High Similarity	NPC469940
0.8551	High Similarity	NPC64466
0.8493	Intermediate Similarity	NPC477918
0.8472	Intermediate Similarity	NPC273366
0.8472	Intermediate Similarity	NPC212733
0.8472	Intermediate Similarity	NPC472311
0.8406	Intermediate Similarity	NPC469724
0.8406	Intermediate Similarity	NPC100917
0.8406	Intermediate Similarity	NPC31187
0.8406	Intermediate Similarity	NPC281203
0.8378	Intermediate Similarity	NPC185465
0.8356	Intermediate Similarity	NPC20466
0.8356	Intermediate Similarity	NPC4209
0.8333	Intermediate Similarity	NPC477930
0.831	Intermediate Similarity	NPC151018
0.831	Intermediate Similarity	NPC320549
0.831	Intermediate Similarity	NPC58057
0.831	Intermediate Similarity	NPC197701
0.831	Intermediate Similarity	NPC156277
0.8289	Intermediate Similarity	NPC12933
0.8267	Intermediate Similarity	NPC320144
0.8267	Intermediate Similarity	NPC192744
0.8243	Intermediate Similarity	NPC66105
0.8243	Intermediate Similarity	NPC477919
0.8243	Intermediate Similarity	NPC475031
0.8243	Intermediate Similarity	NPC317913
0.8243	Intermediate Similarity	NPC143133
0.8243	Intermediate Similarity	NPC474404
0.8243	Intermediate Similarity	NPC298168
0.8243	Intermediate Similarity	NPC264602
0.8243	Intermediate Similarity	NPC207010
0.8243	Intermediate Similarity	NPC180199
0.8219	Intermediate Similarity	NPC179858
0.8219	Intermediate Similarity	NPC477934
0.8205	Intermediate Similarity	NPC319909
0.8194	Intermediate Similarity	NPC232112
0.8194	Intermediate Similarity	NPC310766
0.8158	Intermediate Similarity	NPC472853
0.8158	Intermediate Similarity	NPC477851
0.8143	Intermediate Similarity	NPC474954
0.8143	Intermediate Similarity	NPC470956
0.8133	Intermediate Similarity	NPC80089
0.8133	Intermediate Similarity	NPC329117
0.8133	Intermediate Similarity	NPC324700
0.8133	Intermediate Similarity	NPC476732
0.8133	Intermediate Similarity	NPC171426
0.8133	Intermediate Similarity	NPC199965
0.8133	Intermediate Similarity	NPC321690
0.8133	Intermediate Similarity	NPC224802
0.8133	Intermediate Similarity	NPC34046
0.8125	Intermediate Similarity	NPC474105
0.8125	Intermediate Similarity	NPC151464
0.8125	Intermediate Similarity	NPC143597
0.8108	Intermediate Similarity	NPC246445
0.8108	Intermediate Similarity	NPC477933
0.8108	Intermediate Similarity	NPC477932
0.8088	Intermediate Similarity	NPC128608
0.8082	Intermediate Similarity	NPC254340
0.8082	Intermediate Similarity	NPC472854
0.8028	Intermediate Similarity	NPC324607
0.8028	Intermediate Similarity	NPC327728
0.8028	Intermediate Similarity	NPC131892
0.8028	Intermediate Similarity	NPC321732
0.8028	Intermediate Similarity	NPC213178
0.8028	Intermediate Similarity	NPC6120
0.8026	Intermediate Similarity	NPC52951
0.8026	Intermediate Similarity	NPC201276
0.8026	Intermediate Similarity	NPC80891
0.8	Intermediate Similarity	NPC212661
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC68828
0.8	Intermediate Similarity	NPC471035
0.7973	Intermediate Similarity	NPC195155
0.7973	Intermediate Similarity	NPC174964
0.7973	Intermediate Similarity	NPC97534
0.7973	Intermediate Similarity	NPC21220
0.7973	Intermediate Similarity	NPC125767
0.7971	Intermediate Similarity	NPC230047
0.7971	Intermediate Similarity	NPC19311
0.7971	Intermediate Similarity	NPC469791
0.7969	Intermediate Similarity	NPC184819
0.7949	Intermediate Similarity	NPC30583
0.7949	Intermediate Similarity	NPC289486
0.7949	Intermediate Similarity	NPC61107
0.7945	Intermediate Similarity	NPC244708
0.7945	Intermediate Similarity	NPC161187
0.7945	Intermediate Similarity	NPC330659
0.7945	Intermediate Similarity	NPC474123
0.7922	Intermediate Similarity	NPC261616
0.7917	Intermediate Similarity	NPC476731
0.7867	Intermediate Similarity	NPC472486
0.7867	Intermediate Similarity	NPC475742
0.7867	Intermediate Similarity	NPC472487
0.7867	Intermediate Similarity	NPC5767
0.7848	Intermediate Similarity	NPC15821
0.7848	Intermediate Similarity	NPC472740
0.7821	Intermediate Similarity	NPC77311
0.7821	Intermediate Similarity	NPC147066
0.7821	Intermediate Similarity	NPC58631
0.7821	Intermediate Similarity	NPC469745
0.7812	Intermediate Similarity	NPC53245
0.7812	Intermediate Similarity	NPC288296
0.7808	Intermediate Similarity	NPC89310
0.7792	Intermediate Similarity	NPC158846
0.7792	Intermediate Similarity	NPC472310
0.7778	Intermediate Similarity	NPC302111
0.7763	Intermediate Similarity	NPC23884
0.7763	Intermediate Similarity	NPC221420
0.775	Intermediate Similarity	NPC473336
0.775	Intermediate Similarity	NPC471044
0.7746	Intermediate Similarity	NPC41542
0.7733	Intermediate Similarity	NPC24014
0.7733	Intermediate Similarity	NPC27349
0.7722	Intermediate Similarity	NPC477935
0.7722	Intermediate Similarity	NPC320514
0.7722	Intermediate Similarity	NPC477858
0.7722	Intermediate Similarity	NPC477936
0.7722	Intermediate Similarity	NPC121121
0.7662	Intermediate Similarity	NPC63020
0.7654	Intermediate Similarity	NPC201655
0.7639	Intermediate Similarity	NPC180777
0.7639	Intermediate Similarity	NPC2568
0.7639	Intermediate Similarity	NPC103647
0.7639	Intermediate Similarity	NPC260319
0.7632	Intermediate Similarity	NPC471046
0.7625	Intermediate Similarity	NPC245866
0.7625	Intermediate Similarity	NPC472744
0.7625	Intermediate Similarity	NPC259173
0.76	Intermediate Similarity	NPC133922
0.7595	Intermediate Similarity	NPC201912
0.7595	Intermediate Similarity	NPC38350
0.759	Intermediate Similarity	NPC146937
0.7568	Intermediate Similarity	NPC478227
0.7564	Intermediate Similarity	NPC215843
0.7564	Intermediate Similarity	NPC477371
0.7564	Intermediate Similarity	NPC245029
0.7564	Intermediate Similarity	NPC31302
0.7564	Intermediate Similarity	NPC201459
0.7561	Intermediate Similarity	NPC92139
0.7532	Intermediate Similarity	NPC112463
0.7531	Intermediate Similarity	NPC474996
0.7529	Intermediate Similarity	NPC52756
0.75	Intermediate Similarity	NPC24705
0.75	Intermediate Similarity	NPC72444
0.75	Intermediate Similarity	NPC260956
0.75	Intermediate Similarity	NPC56962
0.75	Intermediate Similarity	NPC159789
0.7468	Intermediate Similarity	NPC470609
0.7467	Intermediate Similarity	NPC36310
0.7467	Intermediate Similarity	NPC279241
0.7439	Intermediate Similarity	NPC76518
0.7439	Intermediate Similarity	NPC29447
0.7439	Intermediate Similarity	NPC294438
0.7439	Intermediate Similarity	NPC264317
0.7436	Intermediate Similarity	NPC478128
0.7436	Intermediate Similarity	NPC26029
0.7412	Intermediate Similarity	NPC77756
0.7407	Intermediate Similarity	NPC471037
0.7407	Intermediate Similarity	NPC168188
0.7407	Intermediate Similarity	NPC69279
0.7407	Intermediate Similarity	NPC167103
0.7407	Intermediate Similarity	NPC83569
0.7407	Intermediate Similarity	NPC470015
0.7403	Intermediate Similarity	NPC104806
0.7381	Intermediate Similarity	NPC474719
0.7375	Intermediate Similarity	NPC472229
0.7375	Intermediate Similarity	NPC472230
0.7375	Intermediate Similarity	NPC477372
0.7375	Intermediate Similarity	NPC103754
0.7375	Intermediate Similarity	NPC232625
0.7375	Intermediate Similarity	NPC474484
0.7368	Intermediate Similarity	NPC255168
0.7361	Intermediate Similarity	NPC189917
0.7361	Intermediate Similarity	NPC96812
0.7361	Intermediate Similarity	NPC168824
0.7361	Intermediate Similarity	NPC39462
0.7361	Intermediate Similarity	NPC107704
0.7356	Intermediate Similarity	NPC470423
0.7353	Intermediate Similarity	NPC162685
0.7353	Intermediate Similarity	NPC476735
0.7349	Intermediate Similarity	NPC80590

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 NPC474962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	3793
0.2-0.3	3554
0.3-0.4	858
0.4-0.5	258
0.5-0.6	235
0.6-0.7	69
0.7-0.8	7
0.8-0.85	17
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD4224	Phase 2
0.9118	High Similarity	NPD6081	Approved
0.8676	High Similarity	NPD5360	Phase 3
0.8676	High Similarity	NPD5361	Clinical (unspecified phase)
0.8592	High Similarity	NPD6113	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD4789	Approved
0.8356	Intermediate Similarity	NPD6117	Approved
0.831	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD6116	Phase 1
0.8235	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4244	Approved
0.8169	Intermediate Similarity	NPD4245	Approved
0.8133	Intermediate Similarity	NPD6118	Approved
0.8133	Intermediate Similarity	NPD6697	Approved
0.8133	Intermediate Similarity	NPD6114	Approved
0.8133	Intermediate Similarity	NPD6115	Approved
0.8056	Intermediate Similarity	NPD5777	Approved
0.8056	Intermediate Similarity	NPD4758	Discontinued
0.8028	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3698	Phase 2
0.7973	Intermediate Similarity	NPD3702	Approved
0.7662	Intermediate Similarity	NPD5364	Discontinued
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7439	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3671	Phase 1
0.7195	Intermediate Similarity	NPD4788	Approved
0.7015	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD3198	Approved
0.697	Remote Similarity	NPD3186	Phase 1
0.6932	Remote Similarity	NPD8035	Phase 2
0.6932	Remote Similarity	NPD8034	Phase 2
0.6905	Remote Similarity	NPD4786	Approved
0.6867	Remote Similarity	NPD4223	Phase 3
0.6867	Remote Similarity	NPD4221	Approved
0.6854	Remote Similarity	NPD6399	Phase 3
0.6824	Remote Similarity	NPD5329	Approved
0.6747	Remote Similarity	NPD4139	Approved
0.6747	Remote Similarity	NPD4692	Approved
0.6744	Remote Similarity	NPD6098	Approved
0.6706	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6623	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6672	Approved
0.6591	Remote Similarity	NPD5737	Approved
0.6591	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD634	Phase 3
0.6559	Remote Similarity	NPD6084	Phase 2
0.6559	Remote Similarity	NPD6083	Phase 2
0.6556	Remote Similarity	NPD5284	Approved
0.6556	Remote Similarity	NPD5281	Approved
0.6552	Remote Similarity	NPD7521	Approved
0.6552	Remote Similarity	NPD5205	Approved
0.6552	Remote Similarity	NPD4693	Phase 3
0.6552	Remote Similarity	NPD7334	Approved
0.6552	Remote Similarity	NPD4690	Approved
0.6552	Remote Similarity	NPD4689	Approved
0.6552	Remote Similarity	NPD4138	Approved
0.6552	Remote Similarity	NPD5330	Approved
0.6552	Remote Similarity	NPD4688	Approved
0.6552	Remote Similarity	NPD6409	Approved
0.6552	Remote Similarity	NPD6684	Approved
0.6552	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD4787	Phase 1
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6673	Approved
0.6517	Remote Similarity	NPD6080	Approved
0.6517	Remote Similarity	NPD5328	Approved
0.6517	Remote Similarity	NPD6904	Approved
0.6517	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3666	Approved
0.6512	Remote Similarity	NPD3665	Phase 1
0.6512	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD8418	Phase 2
0.6413	Remote Similarity	NPD6001	Approved
0.6404	Remote Similarity	NPD5208	Approved
0.6404	Remote Similarity	NPD6903	Approved
0.6374	Remote Similarity	NPD7515	Phase 2
0.6374	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD5280	Approved
0.6364	Remote Similarity	NPD5690	Phase 2
0.6364	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4694	Approved
0.6344	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD4753	Phase 2
0.6329	Remote Similarity	NPD4747	Approved
0.6316	Remote Similarity	NPD5696	Approved
0.6304	Remote Similarity	NPD5133	Approved
0.6237	Remote Similarity	NPD7748	Approved
0.6234	Remote Similarity	NPD375	Phase 2
0.6212	Remote Similarity	NPD345	Approved
0.6212	Remote Similarity	NPD344	Approved
0.6212	Remote Similarity	NPD343	Approved
0.6203	Remote Similarity	NPD4137	Phase 3
0.6196	Remote Similarity	NPD5693	Phase 1
0.6196	Remote Similarity	NPD6050	Approved
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5279	Phase 3
0.6136	Remote Similarity	NPD3668	Phase 3
0.6129	Remote Similarity	NPD4202	Approved
0.6125	Remote Similarity	NPD4691	Approved
0.6118	Remote Similarity	NPD4195	Approved
0.6105	Remote Similarity	NPD7614	Phase 1
0.61	Remote Similarity	NPD5739	Approved
0.61	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD7128	Approved
0.61	Remote Similarity	NPD6675	Approved
0.6098	Remote Similarity	NPD5733	Approved
0.6094	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5692	Phase 3
0.6087	Remote Similarity	NPD5207	Approved
0.6076	Remote Similarity	NPD6705	Phase 1
0.6076	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4243	Approved
0.6047	Remote Similarity	NPD4695	Discontinued
0.6047	Remote Similarity	NPD6928	Phase 2
0.6042	Remote Similarity	NPD5959	Approved
0.6042	Remote Similarity	NPD7902	Approved
0.6022	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD3726	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD3725	Approved
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD4776	Phase 2
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD4777	Suspended
0.6	Remote Similarity	NPD5210	Approved
0.598	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.5979	Remote Similarity	NPD7638	Approved
0.5938	Remote Similarity	NPD2270	Approved
0.5938	Remote Similarity	NPD4697	Phase 3
0.5938	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5222	Approved
0.5938	Remote Similarity	NPD5221	Approved
0.5922	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD6373	Approved
0.5918	Remote Similarity	NPD7639	Approved
0.5918	Remote Similarity	NPD6404	Discontinued
0.5918	Remote Similarity	NPD7640	Approved
0.5914	Remote Similarity	NPD4096	Approved
0.5904	Remote Similarity	NPD4784	Approved
0.5904	Remote Similarity	NPD4687	Approved
0.5904	Remote Similarity	NPD4058	Approved
0.5904	Remote Similarity	NPD4785	Approved
0.5882	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD5697	Approved
0.5876	Remote Similarity	NPD4755	Approved
0.5876	Remote Similarity	NPD5173	Approved
0.5865	Remote Similarity	NPD6883	Approved
0.5865	Remote Similarity	NPD7290	Approved
0.5865	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD7525	Registered
0.5854	Remote Similarity	NPD5276	Approved
0.5833	Remote Similarity	NPD7339	Approved
0.5833	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD6942	Approved
0.5825	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD6847	Approved
0.581	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6650	Approved
0.581	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD8130	Phase 1
0.581	Remote Similarity	NPD6869	Approved
0.58	Remote Similarity	NPD7632	Discontinued
0.5789	Remote Similarity	NPD9656	Approved
0.5784	Remote Similarity	NPD6920	Discontinued
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6014	Approved
0.5769	Remote Similarity	NPD7909	Approved
0.5769	Remote Similarity	NPD6013	Approved
0.5761	Remote Similarity	NPD3573	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5758	Remote Similarity	NPD5286	Approved
0.5758	Remote Similarity	NPD4696	Approved
0.5758	Remote Similarity	NPD5285	Approved
0.5755	Remote Similarity	NPD8297	Approved
0.5755	Remote Similarity	NPD6882	Approved
0.5743	Remote Similarity	NPD6052	Approved
0.5729	Remote Similarity	NPD7900	Approved
0.5729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD8298	Phase 2
0.57	Remote Similarity	NPD5223	Approved
0.5699	Remote Similarity	NPD4518	Approved
0.5688	Remote Similarity	NPD7115	Discovery
0.5682	Remote Similarity	NPD5368	Approved
0.5673	Remote Similarity	NPD6415	Discontinued
0.5672	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4190	Phase 3
0.5647	Remote Similarity	NPD5275	Approved
0.5644	Remote Similarity	NPD5225	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