NPASS Compound

Structure

NPC12728 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 8.4355 5.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5695 2.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7035 3.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4239 3.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7548 0.8964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7035 2.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9239 2.5055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2548 1.7624 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4355 2.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5695 4.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4355 3.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8374 2.0988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3015 2.0988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3015 4.0988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5695 5.0988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7329 1.1043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4457 3.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 10 2 0 0 0 0 3 14 1 0 0 0 0 4 10 1 0 0 0 0 4 15 2 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 27 1 0 0 0 0 8 26 1 0 0 0 0 9 28 1 0 0 0 0 9 29 1 0 0 0 0 12 7 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 8 1 1 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 19 10 1 6 0 0 0 19 26 1 0 0 0 0 20 11 1 6 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	383.493
LogP:	2.386
LogD:	2.811
LogS:	-3.754
# Rotatable Bonds:	4
TPSA:	95.84
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	4.005
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.897
MDCK Permeability:	3.054073386010714e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	93.06379699707031%
Volume Distribution (VD):	0.732
Pgp-substrate:	8.569910049438477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.434
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.713
CYP2D6-inhibitor:	0.542
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	15.667
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.566
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.435
Skin Sensitization:	0.953
Carcinogencity:	0.769
Eye Corrosion:	0.004
Eye Irritation:	0.781
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC12728

Natural Product ID:	NPC12728
*Common Name:**	(1S,2R,5S,6R)-2-(5-Methoxy-3,4-Methylenedioxyphenyl)-6-(3,4-Dihydroxy-5-Methoxyphenyl)-3,7-Dioxabicyclo[3.3.0]Octane
IUPAC Name:	5-[(3R,3aS,6R,6aS)-6-(7-methoxy-1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-3-methoxybenzene-1,2-diol
Synonyms:
Standard InCHIKey:	VVGTYCADBJEFMD-VLSDQLEDSA-N
Standard InCHI:	InChI=1S/C21H22O8/c1-24-15-4-10(3-14(22)18(15)23)19-12-7-27-20(13(12)8-26-19)11-5-16(25-2)21-17(6-11)28-9-29-21/h3-6,12-13,19-20,22-23H,7-9H2,1-2H3/t12-,13-,19+,20+/m1/s1
SMILES:	COc1cc(cc(c1O)O)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376820
PubChem CID:	16215160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499322]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17358082]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547458]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17040	Peperomia duclouxii	Species	Piperaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	3
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	49.8	ug.mL-1	PMID[536086]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	5.3	ug.mL-1	PMID[536086]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	13.2	ug.mL-1	PMID[536086]
NPT2	Others	Unspecified		Activity	=	101.0	%	PMID[536086]
NPT2	Others	Unspecified		Activity	=	105.0	%	PMID[536086]
NPT2	Others	Unspecified		Activity	=	169.0	%	PMID[536086]
NPT2	Others	Unspecified		Activity	=	103.0	%	PMID[536086]
NPT2	Others	Unspecified		Activity	=	92.0	%	PMID[536086]
NPT2	Others	Unspecified		Activity	=	117.0	%	PMID[536086]

☑ 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 NPC12728 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	425
0.1-0.2	1423
0.2-0.3	4019
0.3-0.4	10260
0.4-0.5	8822
0.5-0.6	5434
0.6-0.7	8375
0.7-0.8	2893
0.8-0.85	701
0.85-0.9	261
0.9-0.95	77
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185071
0.9853	High Similarity	NPC255566
0.9853	High Similarity	NPC298317
0.9778	High Similarity	NPC177868
0.9632	High Similarity	NPC46591
0.9568	High Similarity	NPC477702
0.9559	High Similarity	NPC193666
0.9559	High Similarity	NPC123526
0.9559	High Similarity	NPC88640
0.95	High Similarity	NPC212890
0.9489	High Similarity	NPC56091
0.9485	High Similarity	NPC474039
0.9481	High Similarity	NPC24490
0.9481	High Similarity	NPC165155
0.9481	High Similarity	NPC34103
0.9481	High Similarity	NPC49235
0.9481	High Similarity	NPC148893
0.9481	High Similarity	NPC25333
0.9481	High Similarity	NPC141765
0.9407	High Similarity	NPC31530
0.9366	High Similarity	NPC248132
0.9366	High Similarity	NPC130449
0.9357	High Similarity	NPC166884
0.9357	High Similarity	NPC141569
0.9357	High Similarity	NPC118385
0.9357	High Similarity	NPC472713
0.9357	High Similarity	NPC187774
0.9357	High Similarity	NPC477701
0.9357	High Similarity	NPC472712
0.9357	High Similarity	NPC473046
0.9343	High Similarity	NPC283949
0.9338	High Similarity	NPC142547
0.9338	High Similarity	NPC189474
0.9338	High Similarity	NPC150534
0.9338	High Similarity	NPC99572
0.9338	High Similarity	NPC126409
0.9338	High Similarity	NPC135777
0.9301	High Similarity	NPC55158
0.9301	High Similarity	NPC286235
0.9301	High Similarity	NPC51328
0.9286	High Similarity	NPC265154
0.9275	High Similarity	NPC113550
0.9265	High Similarity	NPC326095
0.9265	High Similarity	NPC244983
0.9259	High Similarity	NPC204215
0.9259	High Similarity	NPC72046
0.9259	High Similarity	NPC175067
0.9259	High Similarity	NPC261812
0.9259	High Similarity	NPC65183
0.9225	High Similarity	NPC154971
0.9225	High Similarity	NPC252286
0.9214	High Similarity	NPC5262
0.9214	High Similarity	NPC287124
0.9214	High Similarity	NPC472714
0.9209	High Similarity	NPC226547
0.9203	High Similarity	NPC185908
0.9197	High Similarity	NPC18576
0.9191	High Similarity	NPC266848
0.9191	High Similarity	NPC158331
0.9191	High Similarity	NPC136750
0.9161	High Similarity	NPC39657
0.9155	High Similarity	NPC180953
0.9149	High Similarity	NPC474808
0.9149	High Similarity	NPC477898
0.9143	High Similarity	NPC312199
0.9137	High Similarity	NPC6369
0.9137	High Similarity	NPC30951
0.9137	High Similarity	NPC9068
0.913	High Similarity	NPC121651
0.9124	High Similarity	NPC47181
0.9124	High Similarity	NPC287745
0.9118	High Similarity	NPC471505
0.9097	High Similarity	NPC166584
0.9097	High Similarity	NPC301961
0.9091	High Similarity	NPC226540
0.9085	High Similarity	NPC73467
0.9085	High Similarity	NPC84181
0.9085	High Similarity	NPC121661
0.9078	High Similarity	NPC41782
0.9071	High Similarity	NPC284464
0.9065	High Similarity	NPC101807
0.9058	High Similarity	NPC184938
0.9058	High Similarity	NPC101624
0.9058	High Similarity	NPC236522
0.9051	High Similarity	NPC196937
0.9044	High Similarity	NPC27843
0.9044	High Similarity	NPC115207
0.9044	High Similarity	NPC161557
0.9044	High Similarity	NPC158079
0.9044	High Similarity	NPC40432
0.9044	High Similarity	NPC227160
0.9044	High Similarity	NPC228346
0.9044	High Similarity	NPC7171
0.9044	High Similarity	NPC192255
0.9044	High Similarity	NPC82111
0.9034	High Similarity	NPC668
0.9034	High Similarity	NPC174512
0.9034	High Similarity	NPC293757
0.9034	High Similarity	NPC474965
0.9034	High Similarity	NPC477695
0.9021	High Similarity	NPC197352
0.9021	High Similarity	NPC22150
0.9021	High Similarity	NPC475868
0.9021	High Similarity	NPC469586
0.9021	High Similarity	NPC189239
0.9021	High Similarity	NPC38041
0.9021	High Similarity	NPC279298
0.9021	High Similarity	NPC166506
0.9021	High Similarity	NPC307466
0.9021	High Similarity	NPC110763
0.9007	High Similarity	NPC471908
0.9007	High Similarity	NPC472711
0.8993	High Similarity	NPC25695
0.8993	High Similarity	NPC197166
0.8993	High Similarity	NPC172818
0.8993	High Similarity	NPC11453
0.8986	High Similarity	NPC136757
0.8986	High Similarity	NPC107478
0.898	High Similarity	NPC477699
0.8978	High Similarity	NPC147616
0.8978	High Similarity	NPC4940
0.8978	High Similarity	NPC207400
0.8978	High Similarity	NPC219671
0.8978	High Similarity	NPC106739
0.8978	High Similarity	NPC104077
0.8978	High Similarity	NPC181049
0.8978	High Similarity	NPC259742
0.8973	High Similarity	NPC472709
0.8973	High Similarity	NPC472710
0.8971	High Similarity	NPC233224
0.8971	High Similarity	NPC271208
0.8971	High Similarity	NPC63574
0.8966	High Similarity	NPC71726
0.8963	High Similarity	NPC281864
0.8963	High Similarity	NPC54321
0.8963	High Similarity	NPC328682
0.8958	High Similarity	NPC112861
0.8951	High Similarity	NPC470097
0.8951	High Similarity	NPC114119
0.8951	High Similarity	NPC471415
0.8951	High Similarity	NPC473045
0.8951	High Similarity	NPC25292
0.8951	High Similarity	NPC179521
0.8951	High Similarity	NPC172171
0.8951	High Similarity	NPC239254
0.8944	High Similarity	NPC189115
0.8944	High Similarity	NPC184641
0.8944	High Similarity	NPC474295
0.8944	High Similarity	NPC133934
0.8944	High Similarity	NPC184684
0.8929	High Similarity	NPC469981
0.8913	High Similarity	NPC169973
0.8913	High Similarity	NPC471391
0.8913	High Similarity	NPC471390
0.8913	High Similarity	NPC1474
0.8912	High Similarity	NPC477700
0.8912	High Similarity	NPC475756
0.8905	High Similarity	NPC474017
0.8904	High Similarity	NPC145569
0.8904	High Similarity	NPC240521
0.8904	High Similarity	NPC95392
0.8904	High Similarity	NPC55715
0.8904	High Similarity	NPC216223
0.8904	High Similarity	NPC35877
0.8897	High Similarity	NPC228769
0.8897	High Similarity	NPC470633
0.8897	High Similarity	NPC116019
0.8889	High Similarity	NPC18979
0.8889	High Similarity	NPC178014
0.8889	High Similarity	NPC474749
0.8889	High Similarity	NPC8050
0.8889	High Similarity	NPC473092
0.8889	High Similarity	NPC473093
0.8889	High Similarity	NPC42716
0.8889	High Similarity	NPC11422
0.8881	High Similarity	NPC81638
0.8881	High Similarity	NPC470950
0.8881	High Similarity	NPC473044
0.8881	High Similarity	NPC185307
0.8881	High Similarity	NPC324962
0.8873	High Similarity	NPC469661
0.8873	High Similarity	NPC311530
0.8865	High Similarity	NPC156376
0.8859	High Similarity	NPC159922
0.8851	High Similarity	NPC471154
0.8844	High Similarity	NPC24425
0.8844	High Similarity	NPC473989
0.8841	High Similarity	NPC129687
0.8841	High Similarity	NPC33611
0.8841	High Similarity	NPC158526
0.8841	High Similarity	NPC470270
0.8841	High Similarity	NPC7744
0.8841	High Similarity	NPC100223
0.8841	High Similarity	NPC171928
0.8841	High Similarity	NPC16830
0.8832	High Similarity	NPC187998
0.8832	High Similarity	NPC257582
0.8832	High Similarity	NPC275950
0.8832	High Similarity	NPC77040
0.8832	High Similarity	NPC42300

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 NPC12728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	842
0.2-0.3	1969
0.3-0.4	2895
0.4-0.5	1665
0.5-0.6	984
0.6-0.7	403
0.7-0.8	54
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD3027	Phase 3
0.875	High Similarity	NPD6234	Discontinued
0.8497	Intermediate Similarity	NPD4966	Approved
0.8497	Intermediate Similarity	NPD4965	Approved
0.8497	Intermediate Similarity	NPD4967	Phase 2
0.8365	Intermediate Similarity	NPD7228	Approved
0.8301	Intermediate Similarity	NPD37	Approved
0.8182	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD3705	Approved
0.8085	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7199	Phase 2
0.784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7240	Approved
0.7806	Intermediate Similarity	NPD1653	Approved
0.7805	Intermediate Similarity	NPD3818	Discontinued
0.7733	Intermediate Similarity	NPD7266	Discontinued
0.7698	Intermediate Similarity	NPD1357	Approved
0.7692	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2982	Phase 2
0.7676	Intermediate Similarity	NPD2983	Phase 2
0.7662	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7632	Intermediate Similarity	NPD6674	Discontinued
0.7606	Intermediate Similarity	NPD2981	Phase 2
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.7586	Intermediate Similarity	NPD3018	Phase 2
0.7568	Intermediate Similarity	NPD3620	Phase 2
0.7568	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7054	Approved
0.7535	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7680	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7472	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2861	Phase 2
0.7453	Intermediate Similarity	NPD2978	Approved
0.7453	Intermediate Similarity	NPD2977	Approved
0.7442	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1091	Approved
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7353	Intermediate Similarity	NPD6797	Phase 2
0.7346	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.7262	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6166	Phase 2
0.7261	Intermediate Similarity	NPD5058	Phase 3
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7239	Intermediate Similarity	NPD2801	Approved
0.7219	Intermediate Similarity	NPD4060	Phase 1
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6559	Discontinued
0.7209	Intermediate Similarity	NPD7685	Pre-registration
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1375	Discontinued
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD1558	Phase 1
0.7099	Intermediate Similarity	NPD4005	Discontinued
0.7091	Intermediate Similarity	NPD3817	Phase 2
0.707	Intermediate Similarity	NPD4236	Phase 3
0.707	Intermediate Similarity	NPD4237	Approved
0.7059	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD4675	Approved
0.7055	Intermediate Similarity	NPD4678	Approved
0.7051	Intermediate Similarity	NPD3540	Phase 1
0.7044	Intermediate Similarity	NPD7124	Phase 2
0.7042	Intermediate Similarity	NPD7157	Approved
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7034	Intermediate Similarity	NPD5125	Phase 3
0.7034	Intermediate Similarity	NPD5126	Approved
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7025	Intermediate Similarity	NPD4110	Phase 3
0.7025	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5494	Approved
0.7018	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD4357	Discontinued
0.7	Intermediate Similarity	NPD1511	Approved
0.6987	Remote Similarity	NPD3539	Phase 1
0.6981	Remote Similarity	NPD6190	Approved
0.6981	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3382	Approved
0.697	Remote Similarity	NPD3384	Approved
0.697	Remote Similarity	NPD3383	Approved
0.6968	Remote Similarity	NPD6111	Discontinued
0.6962	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3060	Approved
0.6959	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD4380	Phase 2
0.695	Remote Similarity	NPD7843	Approved
0.6948	Remote Similarity	NPD6355	Discontinued
0.6948	Remote Similarity	NPD5735	Approved
0.6943	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5844	Phase 1
0.6928	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5588	Approved
0.6923	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD6331	Phase 2
0.6914	Remote Similarity	NPD1512	Approved
0.6906	Remote Similarity	NPD2684	Approved
0.6883	Remote Similarity	NPD2238	Phase 2
0.6879	Remote Similarity	NPD2161	Phase 2
0.6875	Remote Similarity	NPD2219	Phase 1
0.6872	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6842	Approved
0.6872	Remote Similarity	NPD6841	Approved
0.6872	Remote Similarity	NPD6843	Phase 3
0.6859	Remote Similarity	NPD4536	Approved
0.6859	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4538	Approved
0.6857	Remote Similarity	NPD4750	Phase 3
0.6855	Remote Similarity	NPD5177	Phase 3
0.6851	Remote Similarity	NPD7296	Approved
0.6839	Remote Similarity	NPD3657	Discovery
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6832	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5536	Phase 2
0.6826	Remote Similarity	NPD8455	Phase 2
0.6824	Remote Similarity	NPD422	Phase 1
0.6823	Remote Similarity	NPD7827	Phase 1
0.6813	Remote Similarity	NPD4628	Phase 3
0.6813	Remote Similarity	NPD3892	Phase 2
0.681	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7075	Discontinued
0.6797	Remote Similarity	NPD7095	Approved
0.6795	Remote Similarity	NPD6653	Approved
0.6792	Remote Similarity	NPD970	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7549	Discontinued
0.6772	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD6099	Approved
0.6765	Remote Similarity	NPD1242	Phase 1
0.6755	Remote Similarity	NPD3094	Phase 2
0.6753	Remote Similarity	NPD5109	Approved
0.6753	Remote Similarity	NPD5111	Phase 2
0.6753	Remote Similarity	NPD5110	Phase 2
0.6752	Remote Similarity	NPD7097	Phase 1
0.675	Remote Similarity	NPD1652	Phase 2
0.6748	Remote Similarity	NPD4123	Phase 3
0.6748	Remote Similarity	NPD2532	Approved
0.6748	Remote Similarity	NPD2534	Approved
0.6748	Remote Similarity	NPD2533	Approved
0.6744	Remote Similarity	NPD3787	Discontinued
0.674	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5124	Phase 1
0.6731	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4210	Discontinued
0.6711	Remote Similarity	NPD6584	Phase 3
0.671	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2674	Phase 3
0.671	Remote Similarity	NPD6233	Phase 2
0.6709	Remote Similarity	NPD5960	Phase 3
0.6708	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4055	Discovery
0.6706	Remote Similarity	NPD5604	Discontinued
0.6691	Remote Similarity	NPD3020	Approved
0.669	Remote Similarity	NPD6671	Approved
0.6689	Remote Similarity	NPD8651	Approved
0.6689	Remote Similarity	NPD6696	Suspended
0.6687	Remote Similarity	NPD7213	Phase 3
0.6687	Remote Similarity	NPD7212	Phase 2
0.6686	Remote Similarity	NPD8127	Discontinued
0.6686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2563	Approved
0.6686	Remote Similarity	NPD2560	Approved
0.6685	Remote Similarity	NPD7906	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD27	Approved
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD2677	Approved
0.6667	Remote Similarity	NPD2489	Approved
0.6648	Remote Similarity	NPD7313	Approved
0.6648	Remote Similarity	NPD4578	Approved
0.6648	Remote Similarity	NPD7311	Approved
0.6648	Remote Similarity	NPD4577	Approved
0.6648	Remote Similarity	NPD7310	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