NPASS Compound

Structure

CID43525 OpenBabel06191715372D 23 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -2.5981 1.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 4.3301 2.5000 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 -3.4641 3.0000 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 1.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.14
Volume:	334.136
LogP:	4.439
LogD:	3.869
LogS:	-3.169
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	2.799
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.3
MDCK Permeability:	1.532289752503857e-05
Pgp-inhibitor:	0.087
Pgp-substrate:	0.165
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.43983459472656%
Volume Distribution (VD):	1.13
Pgp-substrate:	0.9838199019432068%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.561
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.866
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	17.176
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.961
Carcinogencity:	0.087
Eye Corrosion:	0.004
Eye Irritation:	0.919
Respiratory Toxicity:	0.576

Download Data

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

Natural Product: NPC43525

Natural Product ID:	NPC43525
*Common Name:**	5-(Gamma,Gamma-Dimethylallyl)-Oxyresveratrol
IUPAC Name:	4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-6-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	KYQWCQJWDVPXKY-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C19H20O4/c1-12(2)3-5-14-9-15(19(23)11-18(14)22)6-4-13-7-16(20)10-17(21)8-13/h3-4,6-11,20-23H,5H2,1-2H3/b6-4+
SMILES:	CC(=CCc1cc(/C=C/c2cc(O)cc(c2)O)c(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463126
PubChem CID:	11034312
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
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869218]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217294]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	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	2
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	4100.0	nM	PMID[545984]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	36700.0	nM	PMID[545984]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[545984]

☑ 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 NPC43525 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	304
0.1-0.2	1817
0.2-0.3	5047
0.3-0.4	13697
0.4-0.5	4971
0.5-0.6	6064
0.6-0.7	7609
0.7-0.8	2651
0.8-0.85	373
0.85-0.9	117
0.9-0.95	37
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC165770
0.9904	High Similarity	NPC4493
0.9904	High Similarity	NPC225679
0.9904	High Similarity	NPC476632
0.9717	High Similarity	NPC117846
0.9626	High Similarity	NPC107240
0.9615	High Similarity	NPC63698
0.9615	High Similarity	NPC61885
0.9439	High Similarity	NPC166995
0.9364	High Similarity	NPC277588
0.934	High Similarity	NPC33728
0.934	High Similarity	NPC19808
0.9327	High Similarity	NPC292452
0.9327	High Similarity	NPC474839
0.9286	High Similarity	NPC223451
0.9245	High Similarity	NPC174981
0.9238	High Similarity	NPC39664
0.9238	High Similarity	NPC118286
0.9238	High Similarity	NPC109691
0.9238	High Similarity	NPC470700
0.9238	High Similarity	NPC302681
0.9238	High Similarity	NPC39097
0.9231	High Similarity	NPC241891
0.9231	High Similarity	NPC30506
0.9231	High Similarity	NPC102216
0.9231	High Similarity	NPC119860
0.9204	High Similarity	NPC24125
0.9196	High Similarity	NPC191866
0.9167	High Similarity	NPC224527
0.9151	High Similarity	NPC54844
0.9143	High Similarity	NPC134829
0.9143	High Similarity	NPC246056
0.9123	High Similarity	NPC237667
0.9123	High Similarity	NPC476633
0.9107	High Similarity	NPC144343
0.9074	High Similarity	NPC475018
0.9057	High Similarity	NPC248904
0.9038	High Similarity	NPC143659
0.9038	High Similarity	NPC100340
0.9018	High Similarity	NPC470760
0.9009	High Similarity	NPC84999
0.9009	High Similarity	NPC246760
0.9	High Similarity	NPC263753
0.9	High Similarity	NPC261343
0.9	High Similarity	NPC23804
0.8981	High Similarity	NPC202647
0.8972	High Similarity	NPC232523
0.8972	High Similarity	NPC204901
0.8972	High Similarity	NPC158253
0.8966	High Similarity	NPC53567
0.8962	High Similarity	NPC37802
0.8952	High Similarity	NPC146798
0.8952	High Similarity	NPC71002
0.8952	High Similarity	NPC24404
0.8952	High Similarity	NPC106396
0.8952	High Similarity	NPC94351
0.8952	High Similarity	NPC302219
0.8952	High Similarity	NPC242342
0.8952	High Similarity	NPC222522
0.8952	High Similarity	NPC85479
0.8952	High Similarity	NPC313030
0.8952	High Similarity	NPC53051
0.8952	High Similarity	NPC249828
0.8952	High Similarity	NPC168303
0.8942	High Similarity	NPC248573
0.8942	High Similarity	NPC166761
0.8942	High Similarity	NPC161571
0.8942	High Similarity	NPC10588
0.8942	High Similarity	NPC275053
0.8929	High Similarity	NPC115808
0.8899	High Similarity	NPC224870
0.8879	High Similarity	NPC99836
0.8879	High Similarity	NPC12640
0.8879	High Similarity	NPC201662
0.8868	High Similarity	NPC218879
0.8868	High Similarity	NPC244513
0.8868	High Similarity	NPC227458
0.886	High Similarity	NPC217174
0.8857	High Similarity	NPC284011
0.8857	High Similarity	NPC24407
0.8857	High Similarity	NPC11280
0.8857	High Similarity	NPC294186
0.8857	High Similarity	NPC72947
0.8857	High Similarity	NPC166313
0.8857	High Similarity	NPC147310
0.8857	High Similarity	NPC137415
0.8857	High Similarity	NPC192032
0.8846	High Similarity	NPC80027
0.8818	High Similarity	NPC268032
0.8807	High Similarity	NPC299568
0.8807	High Similarity	NPC186385
0.8785	High Similarity	NPC138942
0.8783	High Similarity	NPC69006
0.8774	High Similarity	NPC168829
0.8772	High Similarity	NPC131118
0.875	High Similarity	NPC291789
0.8729	High Similarity	NPC224342
0.8716	High Similarity	NPC95344
0.8692	High Similarity	NPC288411
0.8684	High Similarity	NPC33270
0.8684	High Similarity	NPC474933
0.8684	High Similarity	NPC69261
0.8673	High Similarity	NPC808
0.8655	High Similarity	NPC105031
0.8649	High Similarity	NPC95716
0.8649	High Similarity	NPC151537
0.8632	High Similarity	NPC39029
0.8624	High Similarity	NPC305603
0.8624	High Similarity	NPC61033
0.8611	High Similarity	NPC219286
0.8611	High Similarity	NPC99557
0.8609	High Similarity	NPC190514
0.8609	High Similarity	NPC48781
0.8609	High Similarity	NPC9592
0.8609	High Similarity	NPC206
0.8596	High Similarity	NPC229147
0.8596	High Similarity	NPC141090
0.8596	High Similarity	NPC150624
0.8596	High Similarity	NPC85292
0.8596	High Similarity	NPC261973
0.8596	High Similarity	NPC54507
0.8596	High Similarity	NPC203113
0.8584	High Similarity	NPC473137
0.8584	High Similarity	NPC12656
0.8584	High Similarity	NPC249270
0.8571	High Similarity	NPC46940
0.8571	High Similarity	NPC473521
0.8559	High Similarity	NPC120172
0.8558	High Similarity	NPC274678
0.8558	High Similarity	NPC26244
0.8547	High Similarity	NPC102639
0.8545	High Similarity	NPC58427
0.8545	High Similarity	NPC34864
0.8545	High Similarity	NPC105727
0.8545	High Similarity	NPC114392
0.8534	High Similarity	NPC151197
0.8534	High Similarity	NPC184302
0.8532	High Similarity	NPC271274
0.8532	High Similarity	NPC54765
0.8522	High Similarity	NPC470759
0.8522	High Similarity	NPC219070
0.8522	High Similarity	NPC127894
0.8522	High Similarity	NPC15860
0.8512	High Similarity	NPC252131
0.8509	High Similarity	NPC53906
0.8509	High Similarity	NPC464
0.8509	High Similarity	NPC185541
0.8509	High Similarity	NPC472893
0.85	High Similarity	NPC105925
0.85	High Similarity	NPC113495
0.8496	Intermediate Similarity	NPC319803
0.8476	Intermediate Similarity	NPC473388
0.8468	Intermediate Similarity	NPC58865
0.8462	Intermediate Similarity	NPC475245
0.8462	Intermediate Similarity	NPC128062
0.8462	Intermediate Similarity	NPC151715
0.8462	Intermediate Similarity	NPC472071
0.8462	Intermediate Similarity	NPC282255
0.8462	Intermediate Similarity	NPC76938
0.8455	Intermediate Similarity	NPC254000
0.8455	Intermediate Similarity	NPC151477
0.8455	Intermediate Similarity	NPC176527
0.8443	Intermediate Similarity	NPC28765
0.8435	Intermediate Similarity	NPC114064
0.843	Intermediate Similarity	NPC170485
0.843	Intermediate Similarity	NPC145659
0.843	Intermediate Similarity	NPC9292
0.8426	Intermediate Similarity	NPC168393
0.8426	Intermediate Similarity	NPC108497
0.8421	Intermediate Similarity	NPC276737
0.8421	Intermediate Similarity	NPC228287
0.8421	Intermediate Similarity	NPC22610
0.8421	Intermediate Similarity	NPC180508
0.8417	Intermediate Similarity	NPC97578
0.8411	Intermediate Similarity	NPC225506
0.8403	Intermediate Similarity	NPC77789
0.8403	Intermediate Similarity	NPC18128
0.8396	Intermediate Similarity	NPC77492
0.8393	Intermediate Similarity	NPC296683
0.8393	Intermediate Similarity	NPC44732
0.8393	Intermediate Similarity	NPC13482
0.8387	Intermediate Similarity	NPC15543
0.8387	Intermediate Similarity	NPC282508
0.8381	Intermediate Similarity	NPC32714
0.8378	Intermediate Similarity	NPC11554
0.8378	Intermediate Similarity	NPC262365
0.8365	Intermediate Similarity	NPC295295
0.8364	Intermediate Similarity	NPC469913
0.8362	Intermediate Similarity	NPC195466
0.8362	Intermediate Similarity	NPC50521
0.8362	Intermediate Similarity	NPC221549
0.8362	Intermediate Similarity	NPC244816
0.8361	Intermediate Similarity	NPC236791
0.8361	Intermediate Similarity	NPC282000
0.8361	Intermediate Similarity	NPC293054
0.8361	Intermediate Similarity	NPC324112
0.8361	Intermediate Similarity	NPC74817
0.8361	Intermediate Similarity	NPC246620
0.8361	Intermediate Similarity	NPC169474
0.8361	Intermediate Similarity	NPC124452

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 NPC43525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	1036
0.2-0.3	1376
0.3-0.4	2978
0.4-0.5	1816
0.5-0.6	1091
0.6-0.7	453
0.7-0.8	77
0.8-0.85	14
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD940	Approved
0.9038	High Similarity	NPD846	Approved
0.8942	High Similarity	NPD1242	Phase 1
0.8807	High Similarity	NPD4750	Phase 3
0.8558	High Similarity	NPD2859	Approved
0.8558	High Similarity	NPD2860	Approved
0.8491	Intermediate Similarity	NPD3020	Approved
0.8462	Intermediate Similarity	NPD2933	Approved
0.8462	Intermediate Similarity	NPD2934	Approved
0.8304	Intermediate Similarity	NPD3022	Approved
0.8304	Intermediate Similarity	NPD3021	Approved
0.8208	Intermediate Similarity	NPD844	Approved
0.816	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD7635	Approved
0.808	Intermediate Similarity	NPD4625	Phase 3
0.8037	Intermediate Similarity	NPD1809	Phase 2
0.8019	Intermediate Similarity	NPD845	Approved
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7965	Intermediate Similarity	NPD2342	Discontinued
0.7963	Intermediate Similarity	NPD288	Approved
0.7944	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3027	Phase 3
0.7909	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD1610	Phase 2
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4749	Approved
0.7652	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1613	Approved
0.7615	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD943	Approved
0.7596	Intermediate Similarity	NPD111	Approved
0.7589	Intermediate Similarity	NPD3028	Approved
0.7561	Intermediate Similarity	NPD4589	Approved
0.7559	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3091	Approved
0.7541	Intermediate Similarity	NPD5304	Approved
0.7541	Intermediate Similarity	NPD5303	Approved
0.7538	Intermediate Similarity	NPD6405	Approved
0.7538	Intermediate Similarity	NPD6407	Approved
0.75	Intermediate Similarity	NPD2568	Approved
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7481	Intermediate Similarity	NPD1555	Discontinued
0.748	Intermediate Similarity	NPD4093	Discontinued
0.748	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3094	Phase 2
0.7464	Intermediate Similarity	NPD7390	Discontinued
0.7462	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD422	Phase 1
0.744	Intermediate Similarity	NPD3092	Approved
0.7438	Intermediate Similarity	NPD6671	Approved
0.7419	Intermediate Similarity	NPD2932	Approved
0.7419	Intermediate Similarity	NPD4059	Approved
0.7419	Intermediate Similarity	NPD2286	Discontinued
0.7419	Intermediate Similarity	NPD3019	Approved
0.7417	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2229	Approved
0.7417	Intermediate Similarity	NPD2228	Approved
0.7417	Intermediate Similarity	NPD2234	Approved
0.7377	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1792	Phase 2
0.7364	Intermediate Similarity	NPD2861	Phase 2
0.7355	Intermediate Similarity	NPD497	Approved
0.7348	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7328	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2982	Phase 2
0.7323	Intermediate Similarity	NPD2983	Phase 2
0.7308	Intermediate Similarity	NPD9089	Approved
0.7302	Intermediate Similarity	NPD1201	Approved
0.7286	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD4626	Approved
0.728	Intermediate Similarity	NPD3095	Discontinued
0.7273	Intermediate Similarity	NPD495	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD496	Approved
0.7273	Intermediate Similarity	NPD498	Approved
0.7265	Intermediate Similarity	NPD1445	Approved
0.7265	Intermediate Similarity	NPD1444	Approved
0.7244	Intermediate Similarity	NPD2981	Phase 2
0.7218	Intermediate Similarity	NPD1240	Approved
0.7213	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD9093	Approved
0.7209	Intermediate Similarity	NPD1470	Approved
0.7209	Intermediate Similarity	NPD1133	Approved
0.7209	Intermediate Similarity	NPD1129	Approved
0.7209	Intermediate Similarity	NPD1131	Approved
0.7209	Intermediate Similarity	NPD1164	Approved
0.7209	Intermediate Similarity	NPD1134	Approved
0.7209	Intermediate Similarity	NPD1135	Approved
0.7185	Intermediate Similarity	NPD3553	Approved
0.7185	Intermediate Similarity	NPD3552	Approved
0.7185	Intermediate Similarity	NPD3554	Approved
0.7185	Intermediate Similarity	NPD3555	Approved
0.7155	Intermediate Similarity	NPD9500	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7132	Intermediate Similarity	NPD1510	Phase 2
0.7123	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7330	Discontinued
0.7111	Intermediate Similarity	NPD1607	Approved
0.7111	Intermediate Similarity	NPD4097	Suspended
0.7107	Intermediate Similarity	NPD228	Approved
0.7105	Intermediate Similarity	NPD9273	Approved
0.708	Intermediate Similarity	NPD6100	Approved
0.708	Intermediate Similarity	NPD6099	Approved
0.7054	Intermediate Similarity	NPD4659	Approved
0.705	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD6696	Suspended
0.7	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2561	Approved
0.6977	Remote Similarity	NPD2562	Approved
0.6972	Remote Similarity	NPD7212	Phase 2
0.6972	Remote Similarity	NPD7213	Phase 3
0.697	Remote Similarity	NPD5736	Approved
0.6963	Remote Similarity	NPD2238	Phase 2
0.6953	Remote Similarity	NPD3026	Approved
0.6953	Remote Similarity	NPD3023	Approved
0.6949	Remote Similarity	NPD9610	Approved
0.6949	Remote Similarity	NPD9608	Approved
0.6947	Remote Similarity	NPD3053	Approved
0.6947	Remote Similarity	NPD4103	Phase 2
0.6947	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3055	Approved
0.6942	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5451	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD3025	Approved
0.6929	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1651	Approved
0.6929	Remote Similarity	NPD3024	Approved
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1669	Approved
0.6918	Remote Similarity	NPD4380	Phase 2
0.6911	Remote Similarity	NPD9379	Approved
0.6911	Remote Similarity	NPD5535	Approved
0.6911	Remote Similarity	NPD9377	Approved
0.6909	Remote Similarity	NPD9094	Approved
0.6906	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3540	Phase 1
0.6906	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD602	Approved
0.6894	Remote Similarity	NPD2194	Approved
0.6894	Remote Similarity	NPD859	Approved
0.6894	Remote Similarity	NPD2195	Approved
0.6894	Remote Similarity	NPD599	Approved
0.6894	Remote Similarity	NPD858	Approved
0.6892	Remote Similarity	NPD7819	Suspended
0.6884	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD651	Clinical (unspecified phase)
0.688	Remote Similarity	NPD709	Approved
0.688	Remote Similarity	NPD6387	Discontinued
0.6879	Remote Similarity	NPD3892	Phase 2
0.6879	Remote Similarity	NPD3400	Discontinued
0.687	Remote Similarity	NPD5311	Approved
0.687	Remote Similarity	NPD1283	Approved
0.687	Remote Similarity	NPD5310	Approved
0.687	Remote Similarity	NPD8651	Approved
0.6866	Remote Similarity	NPD5156	Approved
0.6866	Remote Similarity	NPD5155	Approved
0.6864	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2684	Approved
0.6857	Remote Similarity	NPD1549	Phase 2
0.6857	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7041	Phase 2
0.6853	Remote Similarity	NPD1511	Approved
0.6853	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2233	Approved
0.6846	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9269	Phase 2
0.6846	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD2230	Approved
0.6842	Remote Similarity	NPD3637	Approved
0.6842	Remote Similarity	NPD3635	Approved
0.6842	Remote Similarity	NPD3636	Approved
0.6838	Remote Similarity	NPD3059	Approved
0.6838	Remote Similarity	NPD3062	Approved
0.6838	Remote Similarity	NPD3061	Approved
0.6835	Remote Similarity	NPD3539	Phase 1
0.6833	Remote Similarity	NPD968	Approved
0.6824	Remote Similarity	NPD1934	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