NPASS Compound

Structure

CID72529 OpenBabel06191715412D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 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 1.7321 0.0000 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 -1.7321 -2.0000 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 -1.7321 -0.0000 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 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 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 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 12 1 1 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	328.501
LogP:	1.283
LogD:	1.659
LogS:	-3.359
# Rotatable Bonds:	4
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	3.376
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.231
MDCK Permeability:	5.058713213657029e-06
Pgp-inhibitor:	0.646
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	93.26061248779297%
Volume Distribution (VD):	0.553
Pgp-substrate:	6.2676100730896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.331
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.804
CYP2D6-inhibitor:	0.123
CYP2D6-substrate:	0.413
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	9.853
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.563
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.83
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.706
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC72529

Natural Product ID:	NPC72529
*Common Name:**	Isoamericanol A
IUPAC Name:	4-[(2R,3R)-2-(hydroxymethyl)-6-[(E)-3-hydroxyprop-1-enyl]-2,3-dihydro-1,4-benzodioxin-3-yl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	PPZYUSOIUGJLFB-ZHEVZCJESA-N
Standard InCHI:	InChI=1S/C18H18O6/c19-7-1-2-11-3-6-15-16(8-11)24-18(17(10-20)23-15)12-4-5-13(21)14(22)9-12/h1-6,8-9,17-22H,7,10H2/b2-1+/t17-,18-/m1/s1
SMILES:	C(=Cc1ccc2c(c1)O[C@H](c1ccc(c(c1)O)O)[C@@H](CO)O2)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082871
PubChem CID:	6444016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO17957	Solanum sodomeum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17957	Solanum sodomeum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5114	Canis lupus familiaris	Species	Canidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17957	Solanum sodomeum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18517	Phthorimaea operculella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15872	Stachys mucronata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22716	Petalostemon gattingeri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5114	Canis lupus familiaris	Species	Canidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19056	Allium nutans	Species	Amaryllidaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[542271]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	6.0	uM	PMID[542271]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[542271]
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	0.1	uM	PMID[542271]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	9.0	uM	PMID[542271]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[542271]

☑ 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 NPC72529 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	422
0.1-0.2	1589
0.2-0.3	5028
0.3-0.4	12479
0.4-0.5	5168
0.5-0.6	4621
0.6-0.7	7652
0.7-0.8	4249
0.8-0.85	852
0.85-0.9	447
0.9-0.95	170
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC5851
0.9918	High Similarity	NPC86030
0.9754	High Similarity	NPC147821
0.9754	High Similarity	NPC163332
0.9754	High Similarity	NPC319625
0.9754	High Similarity	NPC118787
0.9754	High Similarity	NPC183181
0.9754	High Similarity	NPC292056
0.9754	High Similarity	NPC111247
0.9754	High Similarity	NPC41706
0.9675	High Similarity	NPC474178
0.9675	High Similarity	NPC252307
0.9675	High Similarity	NPC245826
0.9672	High Similarity	NPC191037
0.9672	High Similarity	NPC178284
0.9672	High Similarity	NPC58607
0.959	High Similarity	NPC194519
0.9528	High Similarity	NPC170694
0.9508	High Similarity	NPC114901
0.9508	High Similarity	NPC48990
0.9508	High Similarity	NPC94276
0.9508	High Similarity	NPC109822
0.9508	High Similarity	NPC293701
0.9453	High Similarity	NPC214729
0.9444	High Similarity	NPC472597
0.938	High Similarity	NPC269091
0.938	High Similarity	NPC16435
0.938	High Similarity	NPC306441
0.938	High Similarity	NPC302701
0.938	High Similarity	NPC471665
0.938	High Similarity	NPC471664
0.9375	High Similarity	NPC478085
0.937	High Similarity	NPC470752
0.937	High Similarity	NPC7903
0.937	High Similarity	NPC201587
0.937	High Similarity	NPC16208
0.937	High Similarity	NPC160991
0.937	High Similarity	NPC184447
0.937	High Similarity	NPC253105
0.937	High Similarity	NPC35932
0.9365	High Similarity	NPC472338
0.9344	High Similarity	NPC71090
0.9308	High Similarity	NPC126206
0.9308	High Similarity	NPC470413
0.9308	High Similarity	NPC138738
0.9302	High Similarity	NPC61946
0.9302	High Similarity	NPC47398
0.9302	High Similarity	NPC470356
0.9302	High Similarity	NPC112939
0.9302	High Similarity	NPC112246
0.9302	High Similarity	NPC474206
0.9302	High Similarity	NPC94750
0.9302	High Similarity	NPC260898
0.9302	High Similarity	NPC121812
0.9302	High Similarity	NPC234333
0.9302	High Similarity	NPC164787
0.9291	High Similarity	NPC309787
0.9286	High Similarity	NPC190629
0.9286	High Similarity	NPC222004
0.9286	High Similarity	NPC3439
0.9286	High Similarity	NPC202582
0.9286	High Similarity	NPC273295
0.9286	High Similarity	NPC218856
0.9286	High Similarity	NPC470258
0.9286	High Similarity	NPC285339
0.9286	High Similarity	NPC226788
0.9286	High Similarity	NPC210623
0.928	High Similarity	NPC118533
0.928	High Similarity	NPC165045
0.9268	High Similarity	NPC471693
0.9262	High Similarity	NPC470804
0.9262	High Similarity	NPC127389
0.9262	High Similarity	NPC290451
0.9231	High Similarity	NPC227503
0.9231	High Similarity	NPC474639
0.9231	High Similarity	NPC230734
0.9225	High Similarity	NPC476387
0.9225	High Similarity	NPC310854
0.9225	High Similarity	NPC237594
0.9225	High Similarity	NPC249791
0.9225	High Similarity	NPC119060
0.9219	High Similarity	NPC185604
0.9219	High Similarity	NPC261619
0.9219	High Similarity	NPC61477
0.9219	High Similarity	NPC219876
0.9219	High Similarity	NPC78770
0.9219	High Similarity	NPC15658
0.9219	High Similarity	NPC126029
0.9213	High Similarity	NPC242807
0.9213	High Similarity	NPC174495
0.9213	High Similarity	NPC153739
0.9213	High Similarity	NPC145305
0.9213	High Similarity	NPC42300
0.9213	High Similarity	NPC187998
0.9213	High Similarity	NPC241522
0.9213	High Similarity	NPC257582
0.9213	High Similarity	NPC92164
0.9213	High Similarity	NPC77040
0.9213	High Similarity	NPC64201
0.9167	High Similarity	NPC106944
0.9167	High Similarity	NPC55793
0.916	High Similarity	NPC176051
0.916	High Similarity	NPC211549
0.916	High Similarity	NPC102904
0.916	High Similarity	NPC103976
0.916	High Similarity	NPC326797
0.916	High Similarity	NPC474282
0.916	High Similarity	NPC474390
0.916	High Similarity	NPC107551
0.9154	High Similarity	NPC151224
0.9154	High Similarity	NPC472337
0.9147	High Similarity	NPC229442
0.9147	High Similarity	NPC11060
0.9147	High Similarity	NPC168059
0.9147	High Similarity	NPC263064
0.9147	High Similarity	NPC475840
0.9141	High Similarity	NPC470096
0.9141	High Similarity	NPC268342
0.9141	High Similarity	NPC220825
0.9141	High Similarity	NPC42760
0.9141	High Similarity	NPC30043
0.9141	High Similarity	NPC469613
0.9141	High Similarity	NPC277804
0.9141	High Similarity	NPC470095
0.9141	High Similarity	NPC469625
0.9141	High Similarity	NPC268266
0.9134	High Similarity	NPC475875
0.9134	High Similarity	NPC170844
0.9134	High Similarity	NPC476968
0.9127	High Similarity	NPC474119
0.9127	High Similarity	NPC5428
0.9127	High Similarity	NPC210355
0.912	High Similarity	NPC148627
0.9106	High Similarity	NPC473853
0.9106	High Similarity	NPC262156
0.9106	High Similarity	NPC113865
0.9106	High Similarity	NPC343720
0.9106	High Similarity	NPC54872
0.9106	High Similarity	NPC312675
0.9106	High Similarity	NPC184651
0.9106	High Similarity	NPC470212
0.9106	High Similarity	NPC324571
0.9098	High Similarity	NPC83375
0.9098	High Similarity	NPC224876
0.9098	High Similarity	NPC148615
0.9098	High Similarity	NPC469661
0.9098	High Similarity	NPC177475
0.9098	High Similarity	NPC35071
0.9098	High Similarity	NPC471389
0.9091	High Similarity	NPC22517
0.9084	High Similarity	NPC472336
0.9084	High Similarity	NPC177160
0.9084	High Similarity	NPC156502
0.9084	High Similarity	NPC162659
0.9084	High Similarity	NPC52277
0.9084	High Similarity	NPC77861
0.9084	High Similarity	NPC54743
0.9084	High Similarity	NPC263367
0.9084	High Similarity	NPC29799
0.9084	High Similarity	NPC209985
0.9084	High Similarity	NPC470802
0.9084	High Similarity	NPC477939
0.9084	High Similarity	NPC177035
0.9084	High Similarity	NPC270456
0.9084	High Similarity	NPC248727
0.9084	High Similarity	NPC472334
0.9084	High Similarity	NPC199459
0.9084	High Similarity	NPC265433
0.9084	High Similarity	NPC10737
0.9077	High Similarity	NPC476411
0.9077	High Similarity	NPC187194
0.9077	High Similarity	NPC317380
0.907	High Similarity	NPC127624
0.907	High Similarity	NPC202762
0.907	High Similarity	NPC86655
0.9062	High Similarity	NPC469612
0.9062	High Similarity	NPC469614
0.9062	High Similarity	NPC91291
0.9055	High Similarity	NPC206615
0.9055	High Similarity	NPC282703
0.9055	High Similarity	NPC184733
0.9055	High Similarity	NPC98631
0.9055	High Similarity	NPC21867
0.9055	High Similarity	NPC11258
0.9055	High Similarity	NPC470213
0.9055	High Similarity	NPC186843
0.9055	High Similarity	NPC128208
0.9055	High Similarity	NPC129570
0.9055	High Similarity	NPC470084
0.9055	High Similarity	NPC45774
0.904	High Similarity	NPC122792
0.904	High Similarity	NPC228972
0.9032	High Similarity	NPC209567
0.903	High Similarity	NPC476356
0.903	High Similarity	NPC193722
0.903	High Similarity	NPC469559
0.903	High Similarity	NPC189115
0.903	High Similarity	NPC278469
0.9024	High Similarity	NPC207613
0.9023	High Similarity	NPC309124

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 NPC72529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	859
0.2-0.3	1893
0.3-0.4	2690
0.4-0.5	1580
0.5-0.6	908
0.6-0.7	671
0.7-0.8	173
0.8-0.85	7
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9219	High Similarity	NPD1612	Clinical (unspecified phase)
0.9219	High Similarity	NPD1613	Approved
0.9134	High Similarity	NPD3027	Phase 3
0.8906	High Similarity	NPD1529	Clinical (unspecified phase)
0.8828	High Similarity	NPD1530	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2861	Phase 2
0.8361	Intermediate Similarity	NPD228	Approved
0.8129	Intermediate Similarity	NPD7266	Discontinued
0.8095	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1558	Phase 1
0.808	Intermediate Similarity	NPD5283	Phase 1
0.8077	Intermediate Similarity	NPD1610	Phase 2
0.8077	Intermediate Similarity	NPD1091	Approved
0.8069	Intermediate Similarity	NPD1653	Approved
0.806	Intermediate Similarity	NPD4908	Phase 1
0.8047	Intermediate Similarity	NPD1548	Phase 1
0.8043	Intermediate Similarity	NPD4536	Approved
0.8043	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4538	Approved
0.8014	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5588	Approved
0.7986	Intermediate Similarity	NPD5960	Phase 3
0.7967	Intermediate Similarity	NPD2684	Approved
0.7956	Intermediate Similarity	NPD3620	Phase 2
0.7956	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6674	Discontinued
0.7857	Intermediate Similarity	NPD7843	Approved
0.782	Intermediate Similarity	NPD2983	Phase 2
0.782	Intermediate Similarity	NPD2982	Phase 2
0.7815	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7157	Approved
0.7806	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6166	Phase 2
0.7806	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD968	Approved
0.7803	Intermediate Similarity	NPD3705	Approved
0.78	Intermediate Similarity	NPD2801	Approved
0.7786	Intermediate Similarity	NPD6516	Phase 2
0.7786	Intermediate Similarity	NPD5846	Approved
0.7762	Intermediate Similarity	NPD3060	Approved
0.776	Intermediate Similarity	NPD3022	Approved
0.776	Intermediate Similarity	NPD3021	Approved
0.7746	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2981	Phase 2
0.7742	Intermediate Similarity	NPD290	Approved
0.7724	Intermediate Similarity	NPD5058	Phase 3
0.7721	Intermediate Similarity	NPD3018	Phase 2
0.771	Intermediate Similarity	NPD1357	Approved
0.7698	Intermediate Similarity	NPD4060	Phase 1
0.7674	Intermediate Similarity	NPD6671	Approved
0.7671	Intermediate Similarity	NPD1511	Approved
0.7658	Intermediate Similarity	NPD7054	Approved
0.7655	Intermediate Similarity	NPD6190	Approved
0.7647	Intermediate Similarity	NPD6584	Phase 3
0.7639	Intermediate Similarity	NPD4236	Phase 3
0.7639	Intermediate Similarity	NPD4237	Approved
0.7639	Intermediate Similarity	NPD4162	Approved
0.763	Intermediate Similarity	NPD8651	Approved
0.7626	Intermediate Similarity	NPD6233	Phase 2
0.7623	Intermediate Similarity	NPD291	Approved
0.7619	Intermediate Similarity	NPD4123	Phase 3
0.7612	Intermediate Similarity	NPD2231	Phase 2
0.7612	Intermediate Similarity	NPD2235	Phase 2
0.761	Intermediate Similarity	NPD7472	Approved
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7609	Intermediate Similarity	NPD4625	Phase 3
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD3882	Suspended
0.7568	Intermediate Similarity	NPD1512	Approved
0.7557	Intermediate Similarity	NPD5536	Phase 2
0.7556	Intermediate Similarity	NPD4749	Approved
0.7554	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2677	Approved
0.7518	Intermediate Similarity	NPD5735	Approved
0.7518	Intermediate Similarity	NPD4340	Discontinued
0.7517	Intermediate Similarity	NPD5177	Phase 3
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD4675	Approved
0.7483	Intermediate Similarity	NPD4678	Approved
0.7482	Intermediate Similarity	NPD7095	Approved
0.7469	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3687	Approved
0.7467	Intermediate Similarity	NPD3686	Approved
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7466	Intermediate Similarity	NPD4535	Phase 3
0.7466	Intermediate Similarity	NPD6331	Phase 2
0.7453	Intermediate Similarity	NPD6797	Phase 2
0.7451	Intermediate Similarity	NPD5773	Approved
0.7451	Intermediate Similarity	NPD2978	Approved
0.7451	Intermediate Similarity	NPD2977	Approved
0.7451	Intermediate Similarity	NPD5772	Approved
0.7432	Intermediate Similarity	NPD1774	Approved
0.7432	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6798	Discontinued
0.7426	Intermediate Similarity	NPD6582	Phase 2
0.7426	Intermediate Similarity	NPD6583	Phase 3
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.74	Intermediate Similarity	NPD2122	Discontinued
0.7397	Intermediate Similarity	NPD1652	Phase 2
0.7386	Intermediate Similarity	NPD37	Approved
0.7379	Intermediate Similarity	NPD1375	Discontinued
0.7376	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2674	Phase 3
0.7375	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD4380	Phase 2
0.7362	Intermediate Similarity	NPD7808	Phase 3
0.7361	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4965	Approved
0.7355	Intermediate Similarity	NPD4966	Approved
0.7355	Intermediate Similarity	NPD4967	Phase 2
0.7347	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4110	Phase 3
0.7346	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6653	Approved
0.7338	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD3059	Approved
0.7324	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3062	Approved
0.7324	Intermediate Similarity	NPD3061	Approved
0.7308	Intermediate Similarity	NPD5535	Approved
0.7308	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5241	Discontinued
0.7297	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5762	Approved
0.7259	Intermediate Similarity	NPD9381	Approved
0.7259	Intermediate Similarity	NPD9384	Approved
0.7254	Intermediate Similarity	NPD4062	Phase 3
0.725	Intermediate Similarity	NPD27	Approved
0.725	Intermediate Similarity	NPD2489	Approved
0.7241	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD1182	Approved
0.7234	Intermediate Similarity	NPD3179	Approved
0.7234	Intermediate Similarity	NPD3180	Approved
0.723	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1465	Phase 2
0.7226	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD3054	Approved
0.7222	Intermediate Similarity	NPD5314	Approved
0.7222	Intermediate Similarity	NPD3052	Approved
0.7219	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7526	Approved
0.7219	Intermediate Similarity	NPD52	Approved
0.7214	Intermediate Similarity	NPD9494	Approved
0.7211	Intermediate Similarity	NPD1549	Phase 2
0.7211	Intermediate Similarity	NPD2424	Discontinued
0.7206	Intermediate Similarity	NPD3496	Discontinued
0.7203	Intermediate Similarity	NPD2238	Phase 2
0.7203	Intermediate Similarity	NPD4140	Approved
0.72	Intermediate Similarity	NPD7212	Phase 2
0.72	Intermediate Similarity	NPD7213	Phase 3
0.7195	Intermediate Similarity	NPD7685	Pre-registration
0.7194	Intermediate Similarity	NPD3094	Phase 2
0.7192	Intermediate Similarity	NPD2161	Phase 2
0.719	Intermediate Similarity	NPD4005	Discontinued
0.719	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2969	Approved
0.7188	Intermediate Similarity	NPD2970	Approved
0.7186	Intermediate Similarity	NPD4663	Approved
0.7183	Intermediate Similarity	NPD5718	Phase 2
0.7183	Intermediate Similarity	NPD3145	Approved
0.7183	Intermediate Similarity	NPD3144	Approved
0.7179	Intermediate Similarity	NPD2563	Approved
0.7179	Intermediate Similarity	NPD2560	Approved
0.7176	Intermediate Similarity	NPD821	Approved
0.7174	Intermediate Similarity	NPD5327	Phase 3
0.7172	Intermediate Similarity	NPD7097	Phase 1
0.7153	Intermediate Similarity	NPD5124	Phase 1
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7153	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD3536	Discontinued
0.7152	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD558	Phase 2
0.7133	Intermediate Similarity	NPD3530	Approved
0.7133	Intermediate Similarity	NPD3532	Approved
0.7133	Intermediate Similarity	NPD3531	Approved
0.7132	Intermediate Similarity	NPD5125	Phase 3
0.7132	Intermediate Similarity	NPD5126	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7131	Intermediate Similarity	NPD9296	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