NPASS Compound

Structure

CID225679 OpenBabel06191716022D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 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 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 13 2 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	327.983
LogP:	4.45
LogD:	3.931
LogS:	-3.237
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	2.453
Fsp3:	0.263
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:	-4.936
MDCK Permeability:	1.9019271348952316e-05
Pgp-inhibitor:	0.309
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	98.71736145019531%
Volume Distribution (VD):	1.922
Pgp-substrate:	1.258288025856018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.967
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	17.756
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.955
Carcinogencity:	0.039
Eye Corrosion:	0.021
Eye Irritation:	0.945
Respiratory Toxicity:	0.11

Download Data

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

Natural Product: NPC225679

Natural Product ID:	NPC225679
*Common Name:**	Alpha,Alpha'-Dihydro-3,5,4'-Trihydroxy-5'-Isopentenylstilbene
IUPAC Name:	5-[2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]ethyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	MOQQOXAPDNATKL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O3/c1-13(2)3-7-16-9-14(6-8-19(16)22)4-5-15-10-17(20)12-18(21)11-15/h3,6,8-12,20-22H,4-5,7H2,1-2H3
SMILES:	CC(=CCc1cc(CCc2cc(cc(c2)O)O)ccc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465165
PubChem CID:	10990178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	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.	Activity	=	6.0	10'4/M/s	PMID[474961]

☑ 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 NPC225679 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	312
0.1-0.2	1882
0.2-0.3	5323
0.3-0.4	13591
0.4-0.5	4880
0.5-0.6	6274
0.6-0.7	7499
0.7-0.8	2417
0.8-0.85	353
0.85-0.9	117
0.9-0.95	39
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4493
1.0	High Similarity	NPC476632
1.0	High Similarity	NPC165770
0.9904	High Similarity	NPC43525
0.981	High Similarity	NPC117846
0.9717	High Similarity	NPC107240
0.9709	High Similarity	NPC63698
0.9709	High Similarity	NPC61885
0.9528	High Similarity	NPC166995
0.9429	High Similarity	NPC33728
0.9429	High Similarity	NPC19808
0.9417	High Similarity	NPC474839
0.9333	High Similarity	NPC174981
0.932	High Similarity	NPC241891
0.932	High Similarity	NPC119860
0.932	High Similarity	NPC102216
0.932	High Similarity	NPC30506
0.9273	High Similarity	NPC277588
0.9252	High Similarity	NPC224527
0.9231	High Similarity	NPC292452
0.9231	High Similarity	NPC134829
0.9196	High Similarity	NPC223451
0.9143	High Similarity	NPC248904
0.9143	High Similarity	NPC109691
0.9143	High Similarity	NPC39664
0.9143	High Similarity	NPC302681
0.9143	High Similarity	NPC470700
0.9143	High Similarity	NPC39097
0.9143	High Similarity	NPC118286
0.9126	High Similarity	NPC100340
0.9126	High Similarity	NPC143659
0.9115	High Similarity	NPC24125
0.9107	High Similarity	NPC191866
0.9091	High Similarity	NPC84999
0.9091	High Similarity	NPC246760
0.9083	High Similarity	NPC263753
0.9065	High Similarity	NPC202647
0.9057	High Similarity	NPC54844
0.9057	High Similarity	NPC204901
0.9057	High Similarity	NPC158253
0.9057	High Similarity	NPC232523
0.9048	High Similarity	NPC37802
0.9048	High Similarity	NPC246056
0.9038	High Similarity	NPC242342
0.9038	High Similarity	NPC302219
0.9038	High Similarity	NPC168303
0.9038	High Similarity	NPC249828
0.9038	High Similarity	NPC94351
0.9038	High Similarity	NPC313030
0.9038	High Similarity	NPC53051
0.9038	High Similarity	NPC24404
0.9038	High Similarity	NPC146798
0.9038	High Similarity	NPC222522
0.9038	High Similarity	NPC85479
0.9038	High Similarity	NPC106396
0.9038	High Similarity	NPC71002
0.9035	High Similarity	NPC237667
0.9035	High Similarity	NPC476633
0.9029	High Similarity	NPC161571
0.9029	High Similarity	NPC166761
0.9029	High Similarity	NPC10588
0.9029	High Similarity	NPC248573
0.9029	High Similarity	NPC275053
0.9018	High Similarity	NPC144343
0.8981	High Similarity	NPC475018
0.8981	High Similarity	NPC224870
0.8962	High Similarity	NPC201662
0.8962	High Similarity	NPC12640
0.8962	High Similarity	NPC99836
0.8952	High Similarity	NPC218879
0.8952	High Similarity	NPC244513
0.8952	High Similarity	NPC227458
0.8942	High Similarity	NPC147310
0.8942	High Similarity	NPC72947
0.8942	High Similarity	NPC24407
0.8942	High Similarity	NPC284011
0.8942	High Similarity	NPC137415
0.8942	High Similarity	NPC192032
0.8942	High Similarity	NPC11280
0.8942	High Similarity	NPC294186
0.8942	High Similarity	NPC166313
0.8932	High Similarity	NPC80027
0.8929	High Similarity	NPC470760
0.8909	High Similarity	NPC23804
0.8909	High Similarity	NPC261343
0.8889	High Similarity	NPC299568
0.8889	High Similarity	NPC186385
0.8879	High Similarity	NPC53567
0.8868	High Similarity	NPC138942
0.8857	High Similarity	NPC168829
0.885	High Similarity	NPC131118
0.8839	High Similarity	NPC115808
0.8835	High Similarity	NPC291789
0.8796	High Similarity	NPC95344
0.8774	High Similarity	NPC288411
0.8772	High Similarity	NPC217174
0.8761	High Similarity	NPC33270
0.8761	High Similarity	NPC474933
0.8761	High Similarity	NPC69261
0.875	High Similarity	NPC808
0.8729	High Similarity	NPC105031
0.8727	High Similarity	NPC95716
0.8727	High Similarity	NPC151537
0.8727	High Similarity	NPC268032
0.8704	High Similarity	NPC305603
0.8704	High Similarity	NPC61033
0.8696	High Similarity	NPC69006
0.8692	High Similarity	NPC99557
0.8692	High Similarity	NPC219286
0.8684	High Similarity	NPC190514
0.8684	High Similarity	NPC206
0.8673	High Similarity	NPC85292
0.8673	High Similarity	NPC150624
0.8673	High Similarity	NPC141090
0.8673	High Similarity	NPC54507
0.8673	High Similarity	NPC229147
0.8661	High Similarity	NPC249270
0.8649	High Similarity	NPC46940
0.8649	High Similarity	NPC473521
0.8644	High Similarity	NPC224342
0.8641	High Similarity	NPC26244
0.8641	High Similarity	NPC274678
0.8621	High Similarity	NPC102639
0.8611	High Similarity	NPC54765
0.8611	High Similarity	NPC271274
0.8609	High Similarity	NPC184302
0.8584	High Similarity	NPC53906
0.8584	High Similarity	NPC464
0.8584	High Similarity	NPC185541
0.8571	High Similarity	NPC319803
0.8558	High Similarity	NPC473388
0.8547	High Similarity	NPC39029
0.8545	High Similarity	NPC58865
0.8544	High Similarity	NPC76938
0.8544	High Similarity	NPC128062
0.8544	High Similarity	NPC151715
0.8534	High Similarity	NPC282255
0.8532	High Similarity	NPC176527
0.8532	High Similarity	NPC151477
0.8522	High Similarity	NPC9592
0.8522	High Similarity	NPC48781
0.8509	High Similarity	NPC261973
0.8509	High Similarity	NPC203113
0.8505	High Similarity	NPC168393
0.8505	High Similarity	NPC108497
0.85	High Similarity	NPC170485
0.8496	Intermediate Similarity	NPC180508
0.8496	Intermediate Similarity	NPC12656
0.8496	Intermediate Similarity	NPC276737
0.8496	Intermediate Similarity	NPC22610
0.8496	Intermediate Similarity	NPC228287
0.8496	Intermediate Similarity	NPC473137
0.8491	Intermediate Similarity	NPC225506
0.8476	Intermediate Similarity	NPC77492
0.8475	Intermediate Similarity	NPC120172
0.8468	Intermediate Similarity	NPC13482
0.8468	Intermediate Similarity	NPC296683
0.8462	Intermediate Similarity	NPC32714
0.8455	Intermediate Similarity	NPC34864
0.8455	Intermediate Similarity	NPC262365
0.8455	Intermediate Similarity	NPC105727
0.8455	Intermediate Similarity	NPC11554
0.8455	Intermediate Similarity	NPC58427
0.8455	Intermediate Similarity	NPC114392
0.8448	Intermediate Similarity	NPC151197
0.8447	Intermediate Similarity	NPC295295
0.844	Intermediate Similarity	NPC469913
0.8435	Intermediate Similarity	NPC195466
0.8435	Intermediate Similarity	NPC470759
0.8435	Intermediate Similarity	NPC244816
0.8435	Intermediate Similarity	NPC50521
0.8435	Intermediate Similarity	NPC221549
0.8435	Intermediate Similarity	NPC219070
0.8435	Intermediate Similarity	NPC127894
0.8435	Intermediate Similarity	NPC15860
0.843	Intermediate Similarity	NPC252131
0.8421	Intermediate Similarity	NPC472893
0.8417	Intermediate Similarity	NPC105925
0.8417	Intermediate Similarity	NPC113495
0.8407	Intermediate Similarity	NPC715
0.8396	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC128723
0.8396	Intermediate Similarity	NPC252821
0.8396	Intermediate Similarity	NPC92730
0.8393	Intermediate Similarity	NPC90520
0.8393	Intermediate Similarity	NPC296920
0.8381	Intermediate Similarity	NPC292730
0.8381	Intermediate Similarity	NPC216520
0.8381	Intermediate Similarity	NPC132271
0.8381	Intermediate Similarity	NPC82664
0.8376	Intermediate Similarity	NPC472071
0.8376	Intermediate Similarity	NPC3239
0.8376	Intermediate Similarity	NPC475245
0.8374	Intermediate Similarity	NPC254000
0.8361	Intermediate Similarity	NPC28765
0.8361	Intermediate Similarity	NPC215300
0.835	Intermediate Similarity	NPC204210
0.835	Intermediate Similarity	NPC45040
0.8349	Intermediate Similarity	NPC117115
0.8348	Intermediate Similarity	NPC114064

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 NPC225679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	1057
0.2-0.3	1355
0.3-0.4	2981
0.4-0.5	1793
0.5-0.6	1099
0.6-0.7	441
0.7-0.8	72
0.8-0.85	13
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9126	High Similarity	NPD940	Approved
0.9126	High Similarity	NPD846	Approved
0.9029	High Similarity	NPD1242	Phase 1
0.8889	High Similarity	NPD4750	Phase 3
0.8641	High Similarity	NPD2859	Approved
0.8641	High Similarity	NPD2860	Approved
0.8571	High Similarity	NPD3020	Approved
0.8544	High Similarity	NPD2933	Approved
0.8544	High Similarity	NPD2934	Approved
0.8286	Intermediate Similarity	NPD844	Approved
0.8214	Intermediate Similarity	NPD3022	Approved
0.8214	Intermediate Similarity	NPD3021	Approved
0.8158	Intermediate Similarity	NPD7635	Approved
0.8145	Intermediate Similarity	NPD4625	Phase 3
0.8113	Intermediate Similarity	NPD1809	Phase 2
0.8095	Intermediate Similarity	NPD845	Approved
0.808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD288	Approved
0.8036	Intermediate Similarity	NPD2342	Discontinued
0.8019	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD1610	Phase 2
0.792	Intermediate Similarity	NPD4908	Phase 1
0.7899	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7805	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4749	Approved
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD111	Approved
0.7623	Intermediate Similarity	NPD4589	Approved
0.7619	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD5304	Approved
0.7603	Intermediate Similarity	NPD3091	Approved
0.7603	Intermediate Similarity	NPD5303	Approved
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4093	Discontinued
0.7538	Intermediate Similarity	NPD1613	Approved
0.7538	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD943	Approved
0.7519	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.748	Intermediate Similarity	NPD3019	Approved
0.748	Intermediate Similarity	NPD4059	Approved
0.748	Intermediate Similarity	NPD2286	Discontinued
0.748	Intermediate Similarity	NPD2932	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD2229	Approved
0.7462	Intermediate Similarity	NPD6407	Approved
0.7462	Intermediate Similarity	NPD6405	Approved
0.7458	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1792	Phase 2
0.7424	Intermediate Similarity	NPD2568	Approved
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7422	Intermediate Similarity	NPD3018	Phase 2
0.7405	Intermediate Similarity	NPD1555	Discontinued
0.7402	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD3094	Phase 2
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7379	Intermediate Similarity	NPD9089	Approved
0.736	Intermediate Similarity	NPD1201	Approved
0.7339	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1444	Approved
0.7328	Intermediate Similarity	NPD1445	Approved
0.7295	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD9093	Approved
0.7273	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD497	Approved
0.7273	Intermediate Similarity	NPD1240	Approved
0.7266	Intermediate Similarity	NPD1164	Approved
0.7266	Intermediate Similarity	NPD1134	Approved
0.7266	Intermediate Similarity	NPD1135	Approved
0.7266	Intermediate Similarity	NPD1131	Approved
0.7266	Intermediate Similarity	NPD1133	Approved
0.7266	Intermediate Similarity	NPD1129	Approved
0.7259	Intermediate Similarity	NPD5404	Approved
0.7259	Intermediate Similarity	NPD2935	Discontinued
0.7259	Intermediate Similarity	NPD5406	Approved
0.7259	Intermediate Similarity	NPD5405	Approved
0.7259	Intermediate Similarity	NPD5408	Approved
0.7252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2982	Phase 2
0.7244	Intermediate Similarity	NPD2983	Phase 2
0.7239	Intermediate Similarity	NPD3552	Approved
0.7239	Intermediate Similarity	NPD3553	Approved
0.7239	Intermediate Similarity	NPD3555	Approved
0.7239	Intermediate Similarity	NPD3554	Approved
0.7217	Intermediate Similarity	NPD9500	Approved
0.7214	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1751	Approved
0.72	Intermediate Similarity	NPD3095	Discontinued
0.719	Intermediate Similarity	NPD5283	Phase 1
0.719	Intermediate Similarity	NPD498	Approved
0.719	Intermediate Similarity	NPD496	Approved
0.719	Intermediate Similarity	NPD495	Approved
0.7177	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7330	Discontinued
0.7168	Intermediate Similarity	NPD9273	Approved
0.7167	Intermediate Similarity	NPD228	Approved
0.7165	Intermediate Similarity	NPD2981	Phase 2
0.7164	Intermediate Similarity	NPD4097	Suspended
0.7164	Intermediate Similarity	NPD1607	Approved
0.7132	Intermediate Similarity	NPD6099	Approved
0.7132	Intermediate Similarity	NPD1470	Approved
0.7132	Intermediate Similarity	NPD6100	Approved
0.7109	Intermediate Similarity	NPD4659	Approved
0.7077	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6696	Suspended
0.7031	Intermediate Similarity	NPD2561	Approved
0.7031	Intermediate Similarity	NPD2562	Approved
0.7023	Intermediate Similarity	NPD5736	Approved
0.7015	Intermediate Similarity	NPD2238	Phase 2
0.7009	Intermediate Similarity	NPD9608	Approved
0.7009	Intermediate Similarity	NPD9610	Approved
0.7	Intermediate Similarity	NPD4103	Phase 2
0.7	Intermediate Similarity	NPD3053	Approved
0.7	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3055	Approved
0.7	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5451	Approved
0.6984	Remote Similarity	NPD5691	Approved
0.6984	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1669	Approved
0.6972	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7447	Phase 1
0.6972	Remote Similarity	NPD9094	Approved
0.6967	Remote Similarity	NPD9377	Approved
0.6967	Remote Similarity	NPD9379	Approved
0.6963	Remote Similarity	NPD5124	Phase 1
0.6963	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2194	Approved
0.6947	Remote Similarity	NPD2195	Approved
0.6947	Remote Similarity	NPD599	Approved
0.6947	Remote Similarity	NPD859	Approved
0.6947	Remote Similarity	NPD858	Approved
0.6947	Remote Similarity	NPD602	Approved
0.6942	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD709	Approved
0.6929	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5310	Approved
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD5311	Approved
0.6917	Remote Similarity	NPD5155	Approved
0.6917	Remote Similarity	NPD5156	Approved
0.6917	Remote Similarity	NPD2684	Approved
0.6901	Remote Similarity	NPD7213	Phase 3
0.6901	Remote Similarity	NPD7212	Phase 2
0.6899	Remote Similarity	NPD2232	Approved
0.6899	Remote Similarity	NPD2233	Approved
0.6899	Remote Similarity	NPD2230	Approved
0.6894	Remote Similarity	NPD3636	Approved
0.6894	Remote Similarity	NPD3635	Approved
0.6894	Remote Similarity	NPD3637	Approved
0.6891	Remote Similarity	NPD968	Approved
0.6875	Remote Similarity	NPD1980	Approved
0.6875	Remote Similarity	NPD1981	Approved
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD3143	Discontinued
0.6875	Remote Similarity	NPD3023	Approved
0.687	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD1793	Approved
0.6855	Remote Similarity	NPD1791	Approved
0.685	Remote Similarity	NPD3024	Approved
0.685	Remote Similarity	NPD3025	Approved
0.6849	Remote Similarity	NPD4380	Phase 2
0.6846	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6582	Phase 2
0.6846	Remote Similarity	NPD6583	Phase 3
0.6842	Remote Similarity	NPD2606	Approved
0.6842	Remote Similarity	NPD2605	Approved
0.6835	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3540	Phase 1
0.6835	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5535	Approved
0.6825	Remote Similarity	NPD856	Approved
0.6825	Remote Similarity	NPD16	Approved
0.6824	Remote Similarity	NPD7819	Suspended
0.6818	Remote Similarity	NPD3690	Phase 2
0.6818	Remote Similarity	NPD3691	Phase 2
0.6818	Remote Similarity	NPD4624	Approved
0.6815	Remote Similarity	NPD6663	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)

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