NPASS Compound

Structure

CID270030 OpenBabel06191716072D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.5731 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 0.8827 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 2.5981 -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 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 3.4641 -3.0000 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 5.1962 -4.0000 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 -2.5000 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 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	334.086
LogP:	5.194
LogD:	4.798
LogS:	-4.651
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	2.57
Fsp3:	0.2
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:	-4.974
MDCK Permeability:	1.6945799870882183e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.268
30% Bioavailability (F30%):	0.516

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	99.67627716064453%
Volume Distribution (VD):	1.044
Pgp-substrate:	0.7747040390968323%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.84
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.756
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.869
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.57

ADMET: Excretion

Clearance (CL):	8.116
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.509
Human Hepatotoxicity (H-HT):	0.88
Drug-inuced Liver Injury (DILI):	0.446
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.419
Skin Sensitization:	0.941
Carcinogencity:	0.836
Eye Corrosion:	0.003
Eye Irritation:	0.14
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC270030

Natural Product ID:	NPC270030
*Common Name:**	4-[(E)-2-(5-Methoxy-2,2-Dimethylchromen-7-Yl)Ethenyl]Phenol
IUPAC Name:	4-[(E)-2-(5-methoxy-2,2-dimethylchromen-7-yl)ethenyl]phenol
Synonyms:
Standard InCHIKey:	FQMHTDGEFUNXNZ-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-20(2)11-10-17-18(22-3)12-15(13-19(17)23-20)5-4-14-6-8-16(21)9-7-14/h4-13,21H,1-3H3/b5-4+
SMILES:	CC1(C)C=Cc2c(cc(/C=C/c3ccc(cc3)O)cc2O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463404
PubChem CID:	10542828
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
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5368	Achillea cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2671	Pedicularis semitorta	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12750	Cordia americana	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3890	Scopolia japonica	Species	Solanaceae	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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2680	Individual Protein	Ornithine decarboxylase	Homo sapiens	IC50	=	5200.0	nM	PMID[496480]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[496480]
NPT2	Others	Unspecified		IC50	=	5300.0	nM	PMID[496480]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8500.0	nM	PMID[496480]

☑ 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 NPC270030 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	379
0.1-0.2	1854
0.2-0.3	5353
0.3-0.4	13547
0.4-0.5	3862
0.5-0.6	4391
0.6-0.7	7867
0.7-0.8	4486
0.8-0.85	653
0.85-0.9	267
0.9-0.95	36
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9587	High Similarity	NPC46978
0.9487	High Similarity	NPC137294
0.9487	High Similarity	NPC85895
0.9412	High Similarity	NPC212965
0.9355	High Similarity	NPC474481
0.9333	High Similarity	NPC120638
0.9328	High Similarity	NPC218753
0.9286	High Similarity	NPC36661
0.9174	High Similarity	NPC74137
0.916	High Similarity	NPC184302
0.916	High Similarity	NPC295259
0.9134	High Similarity	NPC469610
0.9106	High Similarity	NPC131397
0.9106	High Similarity	NPC476254
0.9076	High Similarity	NPC190514
0.9076	High Similarity	NPC74821
0.9068	High Similarity	NPC203113
0.906	High Similarity	NPC180508
0.906	High Similarity	NPC228287
0.9055	High Similarity	NPC469611
0.9032	High Similarity	NPC244364
0.9024	High Similarity	NPC159132
0.9016	High Similarity	NPC36016
0.9016	High Similarity	NPC100099
0.9008	High Similarity	NPC102639
0.8992	High Similarity	NPC474933
0.8992	High Similarity	NPC33270
0.8992	High Similarity	NPC69261
0.8983	High Similarity	NPC464
0.8983	High Similarity	NPC185541
0.8976	High Similarity	NPC472590
0.8976	High Similarity	NPC8899
0.8976	High Similarity	NPC160623
0.8968	High Similarity	NPC16577
0.8968	High Similarity	NPC222108
0.8968	High Similarity	NPC96719
0.8968	High Similarity	NPC134360
0.896	High Similarity	NPC149796
0.8952	High Similarity	NPC105031
0.8943	High Similarity	NPC76465
0.8943	High Similarity	NPC96940
0.8943	High Similarity	NPC38761
0.8934	High Similarity	NPC54972
0.8934	High Similarity	NPC476633
0.8908	High Similarity	NPC229147
0.8908	High Similarity	NPC150624
0.8908	High Similarity	NPC85292
0.8908	High Similarity	NPC54507
0.8908	High Similarity	NPC141090
0.8889	High Similarity	NPC280606
0.888	High Similarity	NPC170485
0.888	High Similarity	NPC26879
0.888	High Similarity	NPC283049
0.888	High Similarity	NPC230479
0.888	High Similarity	NPC50315
0.8871	High Similarity	NPC197351
0.8871	High Similarity	NPC106914
0.8871	High Similarity	NPC134195
0.8871	High Similarity	NPC86502
0.8871	High Similarity	NPC246648
0.8862	High Similarity	NPC18128
0.8862	High Similarity	NPC77789
0.8855	High Similarity	NPC35550
0.8837	High Similarity	NPC229442
0.8837	High Similarity	NPC168059
0.8828	High Similarity	NPC211413
0.8828	High Similarity	NPC293203
0.8828	High Similarity	NPC244888
0.8828	High Similarity	NPC118683
0.8828	High Similarity	NPC68205
0.8828	High Similarity	NPC164804
0.8824	High Similarity	NPC808
0.8824	High Similarity	NPC53906
0.8819	High Similarity	NPC472797
0.881	High Similarity	NPC473221
0.8803	High Similarity	NPC90520
0.8803	High Similarity	NPC296920
0.8803	High Similarity	NPC255068
0.88	High Similarity	NPC102540
0.88	High Similarity	NPC188022
0.88	High Similarity	NPC103420
0.88	High Similarity	NPC285040
0.88	High Similarity	NPC17809
0.88	High Similarity	NPC113495
0.878	High Similarity	NPC193364
0.877	High Similarity	NPC8283
0.877	High Similarity	NPC93398
0.877	High Similarity	NPC258979
0.876	High Similarity	NPC472798
0.876	High Similarity	NPC131118
0.875	High Similarity	NPC91291
0.874	High Similarity	NPC222572
0.874	High Similarity	NPC87224
0.874	High Similarity	NPC274717
0.874	High Similarity	NPC215300
0.874	High Similarity	NPC53986
0.874	High Similarity	NPC38604
0.874	High Similarity	NPC38664
0.874	High Similarity	NPC211179
0.8739	High Similarity	NPC22610
0.8739	High Similarity	NPC276737
0.873	High Similarity	NPC276212
0.873	High Similarity	NPC82299
0.872	High Similarity	NPC138248
0.872	High Similarity	NPC228503
0.8718	High Similarity	NPC94045
0.8718	High Similarity	NPC106141
0.8702	High Similarity	NPC151224
0.8692	High Similarity	NPC77196
0.8692	High Similarity	NPC11060
0.8692	High Similarity	NPC92805
0.8682	High Similarity	NPC82503
0.8682	High Similarity	NPC162801
0.8682	High Similarity	NPC471517
0.8678	High Similarity	NPC219070
0.8678	High Similarity	NPC470759
0.8678	High Similarity	NPC50521
0.8678	High Similarity	NPC15860
0.8678	High Similarity	NPC221549
0.8678	High Similarity	NPC244816
0.8678	High Similarity	NPC195466
0.8678	High Similarity	NPC127894
0.8672	High Similarity	NPC472796
0.8672	High Similarity	NPC472795
0.8672	High Similarity	NPC93962
0.8661	High Similarity	NPC53781
0.8661	High Similarity	NPC210355
0.8661	High Similarity	NPC473134
0.8651	High Similarity	NPC82483
0.8651	High Similarity	NPC299584
0.8651	High Similarity	NPC278955
0.8651	High Similarity	NPC234400
0.8651	High Similarity	NPC265483
0.8651	High Similarity	NPC60885
0.8651	High Similarity	NPC105925
0.8651	High Similarity	NPC105718
0.864	High Similarity	NPC474160
0.8636	High Similarity	NPC230734
0.8636	High Similarity	NPC141717
0.8636	High Similarity	NPC474639
0.8636	High Similarity	NPC227503
0.8632	High Similarity	NPC82016
0.8629	High Similarity	NPC75713
0.8626	High Similarity	NPC115335
0.8626	High Similarity	NPC317380
0.8626	High Similarity	NPC106215
0.8626	High Similarity	NPC473107
0.8626	High Similarity	NPC97834
0.8626	High Similarity	NPC223008
0.8626	High Similarity	NPC198154
0.8626	High Similarity	NPC296915
0.8626	High Similarity	NPC225696
0.8615	High Similarity	NPC127624
0.8615	High Similarity	NPC13005
0.8615	High Similarity	NPC202762
0.8615	High Similarity	NPC86655
0.8605	High Similarity	NPC229231
0.8605	High Similarity	NPC214860
0.8595	High Similarity	NPC114064
0.8594	High Similarity	NPC47283
0.8594	High Similarity	NPC39064
0.8594	High Similarity	NPC38017
0.8583	High Similarity	NPC103823
0.8583	High Similarity	NPC214406
0.8583	High Similarity	NPC18924
0.8583	High Similarity	NPC476006
0.8583	High Similarity	NPC44748
0.8583	High Similarity	NPC28730
0.8583	High Similarity	NPC78974
0.8583	High Similarity	NPC223136
0.8571	High Similarity	NPC228972
0.8571	High Similarity	NPC122792
0.8561	High Similarity	NPC474206
0.8561	High Similarity	NPC94750
0.8561	High Similarity	NPC121812
0.8561	High Similarity	NPC164787
0.8561	High Similarity	NPC112246
0.8561	High Similarity	NPC473413
0.8561	High Similarity	NPC112939
0.8561	High Similarity	NPC195022
0.8561	High Similarity	NPC61946
0.8561	High Similarity	NPC470356
0.855	High Similarity	NPC94236
0.855	High Similarity	NPC269528
0.855	High Similarity	NPC85435
0.855	High Similarity	NPC37196
0.855	High Similarity	NPC475840
0.8548	High Similarity	NPC166759
0.854	High Similarity	NPC469557
0.8538	High Similarity	NPC118114
0.8538	High Similarity	NPC196765
0.8538	High Similarity	NPC129106
0.8538	High Similarity	NPC129784
0.8538	High Similarity	NPC228369
0.8538	High Similarity	NPC12875
0.8538	High Similarity	NPC236014
0.8538	High Similarity	NPC476166
0.8538	High Similarity	NPC207892
0.8538	High Similarity	NPC282508
0.8538	High Similarity	NPC280653

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 NPC270030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	1035
0.2-0.3	1633
0.3-0.4	2782
0.4-0.5	1590
0.5-0.6	981
0.6-0.7	636
0.7-0.8	125
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9076	High Similarity	NPD1548	Phase 1
0.8968	High Similarity	NPD4625	Phase 3
0.8943	High Similarity	NPD4749	Approved
0.878	High Similarity	NPD1610	Phase 2
0.874	High Similarity	NPD4908	Phase 1
0.8605	High Similarity	NPD4907	Clinical (unspecified phase)
0.8605	High Similarity	NPD6410	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD422	Phase 1
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2861	Phase 2
0.8162	Intermediate Similarity	NPD6100	Approved
0.8162	Intermediate Similarity	NPD6099	Approved
0.8106	Intermediate Similarity	NPD3027	Phase 3
0.8065	Intermediate Similarity	NPD6671	Approved
0.8045	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3018	Phase 2
0.7949	Intermediate Similarity	NPD1242	Phase 1
0.7869	Intermediate Similarity	NPD4750	Phase 3
0.7832	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD7447	Phase 1
0.7801	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2983	Phase 2
0.7786	Intermediate Similarity	NPD2982	Phase 2
0.7769	Intermediate Similarity	NPD968	Approved
0.7762	Intermediate Similarity	NPD7212	Phase 2
0.7762	Intermediate Similarity	NPD7213	Phase 3
0.7752	Intermediate Similarity	NPD1778	Approved
0.7744	Intermediate Similarity	NPD6584	Phase 3
0.7737	Intermediate Similarity	NPD5124	Phase 1
0.7737	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD846	Approved
0.7731	Intermediate Similarity	NPD940	Approved
0.773	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6696	Suspended
0.771	Intermediate Similarity	NPD2981	Phase 2
0.7681	Intermediate Similarity	NPD1607	Approved
0.7676	Intermediate Similarity	NPD3750	Approved
0.7652	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2801	Approved
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7643	Intermediate Similarity	NPD2796	Approved
0.7639	Intermediate Similarity	NPD1511	Approved
0.7594	Intermediate Similarity	NPD3225	Approved
0.7589	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1510	Phase 2
0.7561	Intermediate Similarity	NPD290	Approved
0.7537	Intermediate Similarity	NPD2797	Approved
0.7536	Intermediate Similarity	NPD1240	Approved
0.7536	Intermediate Similarity	NPD4060	Phase 1
0.7535	Intermediate Similarity	NPD1549	Phase 2
0.7534	Intermediate Similarity	NPD1512	Approved
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6582	Phase 2
0.7519	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.7481	Intermediate Similarity	NPD4626	Approved
0.7467	Intermediate Similarity	NPD1934	Approved
0.746	Intermediate Similarity	NPD228	Approved
0.7447	Intermediate Similarity	NPD7033	Discontinued
0.7432	Intermediate Similarity	NPD1653	Approved
0.7431	Intermediate Similarity	NPD3892	Phase 2
0.7431	Intermediate Similarity	NPD7466	Approved
0.7429	Intermediate Similarity	NPD4097	Suspended
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5535	Approved
0.7373	Intermediate Similarity	NPD2933	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7361	Intermediate Similarity	NPD1652	Phase 2
0.7347	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1398	Phase 1
0.7344	Intermediate Similarity	NPD5283	Phase 1
0.7343	Intermediate Similarity	NPD3540	Phase 1
0.7333	Intermediate Similarity	NPD8651	Approved
0.7324	Intermediate Similarity	NPD3748	Approved
0.7324	Intermediate Similarity	NPD4308	Phase 3
0.732	Intermediate Similarity	NPD3882	Suspended
0.7319	Intermediate Similarity	NPD7095	Approved
0.7313	Intermediate Similarity	NPD1608	Approved
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD844	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.7308	Intermediate Similarity	NPD7340	Approved
0.7303	Intermediate Similarity	NPD7819	Suspended
0.7302	Intermediate Similarity	NPD5451	Approved
0.7293	Intermediate Similarity	NPD3496	Discontinued
0.7286	Intermediate Similarity	NPD1558	Phase 1
0.7286	Intermediate Similarity	NPD2238	Phase 2
0.7273	Intermediate Similarity	NPD3539	Phase 1
0.7273	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD3020	Approved
0.7266	Intermediate Similarity	NPD3268	Approved
0.7266	Intermediate Similarity	NPD7843	Approved
0.7266	Intermediate Similarity	NPD821	Approved
0.7259	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5327	Phase 3
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.7246	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6959	Discontinued
0.7234	Intermediate Similarity	NPD5735	Approved
0.7231	Intermediate Similarity	NPD7157	Approved
0.7226	Intermediate Similarity	NPD4624	Approved
0.7219	Intermediate Similarity	NPD4678	Approved
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7219	Intermediate Similarity	NPD4675	Approved
0.7218	Intermediate Similarity	NPD6516	Phase 2
0.7218	Intermediate Similarity	NPD5846	Approved
0.7211	Intermediate Similarity	NPD6815	Approved
0.7208	Intermediate Similarity	NPD7768	Phase 2
0.7208	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1182	Approved
0.7185	Intermediate Similarity	NPD2235	Phase 2
0.7185	Intermediate Similarity	NPD2230	Approved
0.7185	Intermediate Similarity	NPD2231	Phase 2
0.7185	Intermediate Similarity	NPD2232	Approved
0.7185	Intermediate Similarity	NPD2233	Approved
0.7183	Intermediate Similarity	NPD6353	Approved
0.7171	Intermediate Similarity	NPD7411	Suspended
0.7171	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4140	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7162	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7075	Discontinued
0.7161	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD1651	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4536	Approved
0.7133	Intermediate Similarity	NPD4538	Approved
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4340	Discontinued
0.7111	Intermediate Similarity	NPD1611	Approved
0.7107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6166	Phase 2
0.7107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD288	Approved
0.7105	Intermediate Similarity	NPD6599	Discontinued
0.7101	Intermediate Similarity	NPD3690	Phase 2
0.7101	Intermediate Similarity	NPD3691	Phase 2
0.7099	Intermediate Similarity	NPD2557	Approved
0.7099	Intermediate Similarity	NPD709	Approved
0.709	Intermediate Similarity	NPD17	Approved
0.709	Intermediate Similarity	NPD2667	Approved
0.709	Intermediate Similarity	NPD2668	Approved
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7081	Intermediate Similarity	NPD7054	Approved
0.708	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4628	Phase 3
0.7068	Intermediate Similarity	NPD1894	Discontinued
0.7068	Intermediate Similarity	NPD6581	Approved
0.7068	Intermediate Similarity	NPD6580	Approved
0.7063	Intermediate Similarity	NPD3054	Approved
0.7063	Intermediate Similarity	NPD3052	Approved
0.7055	Intermediate Similarity	NPD7037	Approved
0.7055	Intermediate Similarity	NPD6559	Discontinued
0.705	Intermediate Similarity	NPD4993	Discontinued
0.7047	Intermediate Similarity	NPD4357	Discontinued
0.7045	Intermediate Similarity	NPD3596	Phase 2
0.7042	Intermediate Similarity	NPD4307	Phase 2
0.7037	Intermediate Similarity	NPD7472	Approved
0.7032	Intermediate Similarity	NPD5402	Approved
0.7031	Intermediate Similarity	NPD3022	Approved
0.7031	Intermediate Similarity	NPD3021	Approved
0.7029	Intermediate Similarity	NPD1203	Approved
0.7025	Intermediate Similarity	NPD7199	Phase 2
0.7021	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1296	Phase 2
0.702	Intermediate Similarity	NPD5403	Approved
0.7019	Intermediate Similarity	NPD3818	Discontinued
0.7015	Intermediate Similarity	NPD3444	Approved
0.7015	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3443	Approved
0.7015	Intermediate Similarity	NPD3445	Approved
0.7014	Intermediate Similarity	NPD2200	Suspended
0.7013	Intermediate Similarity	NPD6801	Discontinued
0.7013	Intermediate Similarity	NPD37	Approved
0.7008	Intermediate Similarity	NPD2342	Discontinued
0.7007	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.7	Intermediate Similarity	NPD7635	Approved
0.6994	Remote Similarity	NPD6797	Phase 2
0.6993	Remote Similarity	NPD6355	Discontinued
0.6992	Remote Similarity	NPD5536	Phase 2
0.6987	Remote Similarity	NPD4965	Approved
0.6987	Remote Similarity	NPD4966	Approved
0.6987	Remote Similarity	NPD4967	Phase 2

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