NPASS Compound

Structure

CID328102 OpenBabel06191716202D 32 35 0 0 1 0 0 0 0 0999 V2000 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -1.8171 1.1910 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 5.5000 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 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 1.7321 -0.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 3 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 1.7321 1.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 1.1340 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 -1.8171 2.8090 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 25 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 31 1 0 0 0 0 13 16 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 28 1 0 0 0 0 22 29 2 0 0 0 0 23 32 1 0 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	444.534
LogP:	4.899
LogD:	2.677
LogS:	-2.82
# Rotatable Bonds:	4
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	3.782
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	1.1045884093618952e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.252
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	94.34649658203125%
Volume Distribution (VD):	0.596
Pgp-substrate:	5.967096328735352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.26
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	5.82
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.595
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.911
Carcinogencity:	0.223
Eye Corrosion:	0.003
Eye Irritation:	0.243
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC328102

Natural Product ID:	NPC328102
*Common Name:**	(+/-)-Furowanin B
IUPAC Name:	3-(3,4-dihydroxyphenyl)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(3-methylbut-2-enyl)-8,9-dihydrofuro[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	YOKJEIDBLPWOSL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O7/c1-12(2)5-7-14-21(28)20-22(29)16(13-6-8-17(26)18(27)9-13)11-31-24(20)15-10-19(25(3,4)30)32-23(14)15/h5-6,8-9,11,19,26-28,30H,7,10H2,1-4H3
SMILES:	CC(=CCC1=C2C(=C3C(=C1O)C(=O)C(=CO3)C4=CC(=C(C=C4)O)O)CC(O2)C(C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491885
PubChem CID:	11655056
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22654	Millettia pachycarpa	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	13000.0	nM	PMID[463225]

☑ 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 NPC328102 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	430
0.1-0.2	1636
0.2-0.3	3776
0.3-0.4	9606
0.4-0.5	8830
0.5-0.6	3659
0.6-0.7	4904
0.7-0.8	5132
0.8-0.85	2482
0.85-0.9	1599
0.9-0.95	617
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC472624
0.9677	High Similarity	NPC124038
0.9615	High Similarity	NPC300053
0.9615	High Similarity	NPC108433
0.9613	High Similarity	NPC81679
0.9613	High Similarity	NPC472635
0.961	High Similarity	NPC476283
0.961	High Similarity	NPC119209
0.961	High Similarity	NPC192686
0.961	High Similarity	NPC118256
0.9608	High Similarity	NPC291508
0.9608	High Similarity	NPC27337
0.9605	High Similarity	NPC234255
0.9603	High Similarity	NPC31627
0.9603	High Similarity	NPC327269
0.9603	High Similarity	NPC476238
0.9557	High Similarity	NPC288813
0.9551	High Similarity	NPC472582
0.9548	High Similarity	NPC474038
0.9545	High Similarity	NPC74178
0.9545	High Similarity	NPC184755
0.9542	High Similarity	NPC291878
0.9542	High Similarity	NPC35038
0.9542	High Similarity	NPC195796
0.9542	High Similarity	NPC472455
0.9542	High Similarity	NPC282307
0.9542	High Similarity	NPC170026
0.9542	High Similarity	NPC278778
0.9539	High Similarity	NPC74924
0.9539	High Similarity	NPC213896
0.9539	High Similarity	NPC192083
0.9536	High Similarity	NPC154345
0.9536	High Similarity	NPC471675
0.949	High Similarity	NPC472277
0.9487	High Similarity	NPC474034
0.9487	High Similarity	NPC474033
0.9484	High Similarity	NPC475784
0.9484	High Similarity	NPC476980
0.9481	High Similarity	NPC472598
0.9481	High Similarity	NPC284820
0.9481	High Similarity	NPC52889
0.9481	High Similarity	NPC474055
0.9481	High Similarity	NPC471209
0.9481	High Similarity	NPC473272
0.9477	High Similarity	NPC45849
0.9477	High Similarity	NPC321779
0.9477	High Similarity	NPC472280
0.9477	High Similarity	NPC200761
0.9477	High Similarity	NPC470327
0.9477	High Similarity	NPC477503
0.9474	High Similarity	NPC324233
0.9474	High Similarity	NPC471982
0.9474	High Similarity	NPC323626
0.9474	High Similarity	NPC473996
0.9474	High Similarity	NPC237994
0.9474	High Similarity	NPC106976
0.9474	High Similarity	NPC285623
0.947	High Similarity	NPC3825
0.947	High Similarity	NPC88804
0.947	High Similarity	NPC472421
0.9434	High Similarity	NPC165456
0.943	High Similarity	NPC119589
0.943	High Similarity	NPC235610
0.9427	High Similarity	NPC205265
0.9427	High Similarity	NPC472281
0.9427	High Similarity	NPC18100
0.9427	High Similarity	NPC186686
0.9427	High Similarity	NPC472625
0.9423	High Similarity	NPC472634
0.9423	High Similarity	NPC471210
0.9423	High Similarity	NPC26326
0.9423	High Similarity	NPC472632
0.9423	High Similarity	NPC134783
0.9423	High Similarity	NPC187354
0.9419	High Similarity	NPC117418
0.9419	High Similarity	NPC204879
0.9419	High Similarity	NPC22192
0.9419	High Similarity	NPC53545
0.9416	High Similarity	NPC209614
0.9416	High Similarity	NPC470328
0.9416	High Similarity	NPC472626
0.9416	High Similarity	NPC471985
0.9412	High Similarity	NPC170492
0.9412	High Similarity	NPC298692
0.9412	High Similarity	NPC18727
0.9408	High Similarity	NPC474772
0.9408	High Similarity	NPC472423
0.9408	High Similarity	NPC474744
0.9408	High Similarity	NPC472580
0.9408	High Similarity	NPC472636
0.9408	High Similarity	NPC256406
0.9404	High Similarity	NPC171916
0.9404	High Similarity	NPC38545
0.9375	High Similarity	NPC472276
0.9363	High Similarity	NPC474150
0.9363	High Similarity	NPC261470
0.9363	High Similarity	NPC472448
0.9363	High Similarity	NPC194427
0.9363	High Similarity	NPC474162
0.9363	High Similarity	NPC476247
0.9363	High Similarity	NPC83922
0.9359	High Similarity	NPC174953
0.9359	High Similarity	NPC472631
0.9359	High Similarity	NPC36217
0.9359	High Similarity	NPC472630
0.9359	High Similarity	NPC28241
0.9359	High Similarity	NPC282009
0.9359	High Similarity	NPC287328
0.9355	High Similarity	NPC474681
0.9355	High Similarity	NPC78071
0.9355	High Similarity	NPC476981
0.9355	High Similarity	NPC223787
0.9355	High Similarity	NPC218313
0.9355	High Similarity	NPC67876
0.9351	High Similarity	NPC133392
0.9351	High Similarity	NPC226025
0.9351	High Similarity	NPC117992
0.9351	High Similarity	NPC152951
0.9351	High Similarity	NPC57674
0.9351	High Similarity	NPC230149
0.9351	High Similarity	NPC256925
0.9351	High Similarity	NPC168247
0.9346	High Similarity	NPC60972
0.9346	High Similarity	NPC39732
0.9346	High Similarity	NPC302950
0.9346	High Similarity	NPC219582
0.9346	High Similarity	NPC157784
0.9346	High Similarity	NPC236637
0.9346	High Similarity	NPC477957
0.9346	High Similarity	NPC63187
0.9346	High Similarity	NPC37684
0.9338	High Similarity	NPC203077
0.9338	High Similarity	NPC168085
0.9338	High Similarity	NPC238279
0.9338	High Similarity	NPC166036
0.9308	High Similarity	NPC170245
0.9308	High Similarity	NPC43319
0.9304	High Similarity	NPC473313
0.9304	High Similarity	NPC472278
0.9304	High Similarity	NPC329669
0.9299	High Similarity	NPC167678
0.9299	High Similarity	NPC198829
0.9299	High Similarity	NPC258331
0.9299	High Similarity	NPC142252
0.9299	High Similarity	NPC259456
0.9299	High Similarity	NPC471499
0.9299	High Similarity	NPC94155
0.9299	High Similarity	NPC471212
0.9299	High Similarity	NPC289771
0.9299	High Similarity	NPC29876
0.9299	High Similarity	NPC471211
0.9295	High Similarity	NPC469658
0.9295	High Similarity	NPC473990
0.9295	High Similarity	NPC187792
0.9295	High Similarity	NPC250214
0.9295	High Similarity	NPC95936
0.9295	High Similarity	NPC210459
0.929	High Similarity	NPC133970
0.929	High Similarity	NPC24640
0.929	High Similarity	NPC471500
0.929	High Similarity	NPC5322
0.929	High Similarity	NPC6633
0.929	High Similarity	NPC276444
0.9286	High Similarity	NPC33051
0.9286	High Similarity	NPC227337
0.9286	High Similarity	NPC223701
0.9286	High Similarity	NPC472583
0.9286	High Similarity	NPC141212
0.9286	High Similarity	NPC7989
0.9286	High Similarity	NPC49402
0.9286	High Similarity	NPC273462
0.9286	High Similarity	NPC70433
0.9286	High Similarity	NPC189130
0.9281	High Similarity	NPC59162
0.9281	High Similarity	NPC472420
0.9281	High Similarity	NPC205046
0.9281	High Similarity	NPC263384
0.9281	High Similarity	NPC244577
0.9281	High Similarity	NPC472422
0.9281	High Similarity	NPC304295
0.9281	High Similarity	NPC471676
0.9276	High Similarity	NPC183950
0.9276	High Similarity	NPC223579
0.9276	High Similarity	NPC177298
0.9276	High Similarity	NPC317492
0.9276	High Similarity	NPC137062
0.9276	High Similarity	NPC1612
0.9276	High Similarity	NPC52005
0.9276	High Similarity	NPC287101
0.9276	High Similarity	NPC183959
0.9276	High Similarity	NPC48479
0.9272	High Similarity	NPC108406
0.9272	High Similarity	NPC14875
0.9259	High Similarity	NPC310794
0.925	High Similarity	NPC218226
0.925	High Similarity	NPC150131
0.9245	High Similarity	NPC62261
0.9245	High Similarity	NPC50960
0.9245	High Similarity	NPC293319
0.9245	High Similarity	NPC326520

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 NPC328102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	929
0.2-0.3	1738
0.3-0.4	2622
0.4-0.5	1897
0.5-0.6	999
0.6-0.7	410
0.7-0.8	128
0.8-0.85	35
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD2393	Clinical (unspecified phase)
0.9346	High Similarity	NPD1934	Approved
0.9167	High Similarity	NPD3882	Suspended
0.9161	High Similarity	NPD2801	Approved
0.913	High Similarity	NPD3818	Discontinued
0.9073	High Similarity	NPD1511	Approved
0.8968	High Similarity	NPD4380	Phase 2
0.8954	High Similarity	NPD1512	Approved
0.8889	High Similarity	NPD6167	Clinical (unspecified phase)
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD6166	Phase 2
0.8889	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD5494	Approved
0.875	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD3817	Phase 2
0.8727	High Similarity	NPD7054	Approved
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD7074	Phase 3
0.8675	High Similarity	NPD7472	Approved
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8623	High Similarity	NPD6797	Phase 2
0.8618	High Similarity	NPD1549	Phase 2
0.8616	High Similarity	NPD6801	Discontinued
0.8609	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD7251	Discontinued
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.8543	High Similarity	NPD1510	Phase 2
0.8462	Intermediate Similarity	NPD6559	Discontinued
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7808	Phase 3
0.8395	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD1247	Approved
0.8354	Intermediate Similarity	NPD919	Approved
0.8344	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8313	Intermediate Similarity	NPD6232	Discontinued
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8278	Intermediate Similarity	NPD1240	Approved
0.8274	Intermediate Similarity	NPD7473	Discontinued
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5402	Approved
0.817	Intermediate Similarity	NPD1607	Approved
0.8158	Intermediate Similarity	NPD943	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8089	Intermediate Similarity	NPD2800	Approved
0.8075	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD920	Approved
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8039	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1613	Approved
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1243	Approved
0.7964	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5401	Approved
0.795	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD230	Phase 1
0.7843	Intermediate Similarity	NPD3027	Phase 3
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2313	Discontinued
0.767	Intermediate Similarity	NPD5953	Discontinued
0.7669	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD447	Suspended
0.7637	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD37	Approved
0.7611	Intermediate Similarity	NPD8434	Phase 2
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD7033	Discontinued
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1653	Approved
0.7588	Intermediate Similarity	NPD4965	Approved
0.7588	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD4967	Phase 2
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6099	Approved
0.7562	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD2309	Approved
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7228	Approved
0.7487	Intermediate Similarity	NPD7584	Approved
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9494	Approved
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD5711	Approved
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD7390	Discontinued
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8313	Approved
0.7444	Intermediate Similarity	NPD8312	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1933	Approved
0.7419	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4361	Phase 2
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7362	Intermediate Similarity	NPD2424	Discontinued
0.7355	Intermediate Similarity	NPD1203	Approved
0.7354	Intermediate Similarity	NPD6778	Approved
0.7354	Intermediate Similarity	NPD6779	Approved
0.7354	Intermediate Similarity	NPD6782	Approved
0.7354	Intermediate Similarity	NPD6776	Approved
0.7354	Intermediate Similarity	NPD6781	Approved
0.7354	Intermediate Similarity	NPD6777	Approved
0.7354	Intermediate Similarity	NPD6780	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7318	Intermediate Similarity	NPD1729	Discontinued
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7312	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2403	Approved
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7284	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD5761	Phase 2
0.7267	Intermediate Similarity	NPD5760	Phase 2
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7435	Discontinued
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7232	Intermediate Similarity	NPD5242	Approved
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7212	Intermediate Similarity	NPD2654	Approved
0.7209	Intermediate Similarity	NPD6844	Discontinued
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3823	Discontinued
0.7161	Intermediate Similarity	NPD9269	Phase 2
0.7161	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.715	Intermediate Similarity	NPD7696	Phase 3
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7113	Intermediate Similarity	NPD7871	Phase 2
0.7113	Intermediate Similarity	NPD7870	Phase 2
0.7111	Intermediate Similarity	NPD2163	Approved
0.7111	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1652	Phase 2
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7701	Phase 2
0.7092	Intermediate Similarity	NPD7585	Approved
0.7091	Intermediate Similarity	NPD7266	Discontinued
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.709	Intermediate Similarity	NPD6534	Approved
0.709	Intermediate Similarity	NPD6535	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