NPASS Compound

Structure

NPC471665 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 2.5981 0.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -3.4641 -0.0000 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 0.8660 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 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 5 2 0 0 0 0 1 10 1 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 24 1 0 0 0 0 16 9 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 11 1 1 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	1.745
LogD:	1.299
LogS:	-4.248
# Rotatable Bonds:	4
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	3.261
Fsp3:	0.167
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:	-5.285
MDCK Permeability:	9.443457201996353e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	89.68879699707031%
Volume Distribution (VD):	0.299
Pgp-substrate:	5.325528144836426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	9.534
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.212
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.792
Carcinogencity:	0.766
Eye Corrosion:	0.004
Eye Irritation:	0.816
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC471665

Natural Product ID:	NPC471665
*Common Name:**	Rel-Americanoic Acid A
IUPAC Name:	(E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	FFMAMRFQOOHFDW-SOPWNFQTSA-N
Standard InCHI:	InChI=1S/C18H16O7/c19-9-16-18(11-3-4-12(20)13(21)8-11)25-14-5-1-10(2-6-17(22)23)7-15(14)24-16/h1-8,16,18-21H,9H2,(H,22,23)/b6-2+/t16-,18-/m0/s1
SMILES:	OC[C@@H]1Oc2cc(/C=C/C(=O)O)ccc2O[C@H]1c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3088127
PubChem CID:	76309919
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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[505680]

☑ 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 NPC471665 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	325
0.1-0.2	1460
0.2-0.3	4276
0.3-0.4	9866
0.4-0.5	8182
0.5-0.6	3711
0.6-0.7	7556
0.7-0.8	5943
0.8-0.85	1059
0.85-0.9	259
0.9-0.95	54
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471664
0.9923	High Similarity	NPC126206
0.9618	High Similarity	NPC214729
0.9542	High Similarity	NPC135127
0.9412	High Similarity	NPC478239
0.9407	High Similarity	NPC186406
0.9394	High Similarity	NPC237594
0.9394	High Similarity	NPC249791
0.9394	High Similarity	NPC476387
0.9394	High Similarity	NPC119060
0.938	High Similarity	NPC72529
0.9343	High Similarity	NPC232228
0.9338	High Similarity	NPC157816
0.9338	High Similarity	NPC140502
0.9308	High Similarity	NPC5851
0.9308	High Similarity	NPC86030
0.9281	High Similarity	NPC476347
0.9275	High Similarity	NPC274960
0.9275	High Similarity	NPC473909
0.9275	High Similarity	NPC143120
0.9265	High Similarity	NPC83375
0.9265	High Similarity	NPC224876
0.9214	High Similarity	NPC476348
0.9214	High Similarity	NPC187398
0.9209	High Similarity	NPC199928
0.9203	High Similarity	NPC292443
0.9197	High Similarity	NPC193722
0.9197	High Similarity	NPC278469
0.9191	High Similarity	NPC202700
0.9154	High Similarity	NPC319625
0.9154	High Similarity	NPC163332
0.9154	High Similarity	NPC292056
0.9154	High Similarity	NPC41706
0.9154	High Similarity	NPC111247
0.9154	High Similarity	NPC147821
0.9154	High Similarity	NPC183181
0.9154	High Similarity	NPC118787
0.9149	High Similarity	NPC476394
0.9149	High Similarity	NPC98809
0.9149	High Similarity	NPC106138
0.9137	High Similarity	NPC252292
0.9137	High Similarity	NPC163898
0.9137	High Similarity	NPC476864
0.9137	High Similarity	NPC476868
0.9137	High Similarity	NPC476869
0.9137	High Similarity	NPC100998
0.9137	High Similarity	NPC476866
0.9137	High Similarity	NPC476382
0.9137	High Similarity	NPC34927
0.9137	High Similarity	NPC34587
0.9118	High Similarity	NPC100389
0.9111	High Similarity	NPC186418
0.9085	High Similarity	NPC120426
0.9085	High Similarity	NPC21184
0.9085	High Similarity	NPC205727
0.9085	High Similarity	NPC294522
0.9084	High Similarity	NPC245826
0.9084	High Similarity	NPC252307
0.9084	High Similarity	NPC474178
0.9077	High Similarity	NPC213552
0.9077	High Similarity	NPC120225
0.9077	High Similarity	NPC178284
0.9077	High Similarity	NPC191037
0.9077	High Similarity	NPC58607
0.9071	High Similarity	NPC476865
0.9071	High Similarity	NPC268515
0.9071	High Similarity	NPC40222
0.9065	High Similarity	NPC476867
0.9058	High Similarity	NPC67467
0.9051	High Similarity	NPC267291
0.9014	High Similarity	NPC176903
0.9014	High Similarity	NPC30688
0.9014	High Similarity	NPC475250
0.9007	High Similarity	NPC232992
0.9	High Similarity	NPC289459
0.9	High Similarity	NPC194519
0.8971	High Similarity	NPC471719
0.8971	High Similarity	NPC37468
0.8971	High Similarity	NPC157554
0.8963	High Similarity	NPC287597
0.8963	High Similarity	NPC34293
0.8963	High Similarity	NPC170694
0.8963	High Similarity	NPC886
0.8963	High Similarity	NPC111635
0.8963	High Similarity	NPC67247
0.8951	High Similarity	NPC259576
0.8951	High Similarity	NPC221091
0.8944	High Similarity	NPC472969
0.8944	High Similarity	NPC478237
0.8929	High Similarity	NPC160378
0.8929	High Similarity	NPC110063
0.8923	High Similarity	NPC246704
0.8923	High Similarity	NPC293701
0.8923	High Similarity	NPC94276
0.8923	High Similarity	NPC48990
0.8923	High Similarity	NPC109822
0.8923	High Similarity	NPC114901
0.8905	High Similarity	NPC138738
0.8905	High Similarity	NPC470413
0.8905	High Similarity	NPC78363
0.8889	High Similarity	NPC36490
0.8889	High Similarity	NPC300329
0.8881	High Similarity	NPC94871
0.8881	High Similarity	NPC306890
0.8881	High Similarity	NPC259347
0.8881	High Similarity	NPC476398
0.8881	High Similarity	NPC472597
0.8881	High Similarity	NPC476386
0.8881	High Similarity	NPC473427
0.8881	High Similarity	NPC471062
0.8881	High Similarity	NPC470933
0.8873	High Similarity	NPC15577
0.8872	High Similarity	NPC83062
0.8865	High Similarity	NPC262182
0.8865	High Similarity	NPC216819
0.8865	High Similarity	NPC287615
0.8865	High Similarity	NPC83743
0.8855	High Similarity	NPC87113
0.8846	High Similarity	NPC279379
0.8841	High Similarity	NPC226005
0.8837	High Similarity	NPC147654
0.8832	High Similarity	NPC302701
0.8832	High Similarity	NPC16435
0.8832	High Similarity	NPC471988
0.8832	High Similarity	NPC306441
0.8832	High Similarity	NPC120852
0.8832	High Similarity	NPC269091
0.8828	High Similarity	NPC163598
0.8828	High Similarity	NPC264875
0.8828	High Similarity	NPC120774
0.8824	High Similarity	NPC309744
0.8824	High Similarity	NPC478085
0.8819	High Similarity	NPC470934
0.8819	High Similarity	NPC476871
0.8819	High Similarity	NPC257970
0.8819	High Similarity	NPC188393
0.8819	High Similarity	NPC470927
0.8815	High Similarity	NPC245120
0.8815	High Similarity	NPC7903
0.8815	High Similarity	NPC253105
0.8815	High Similarity	NPC470752
0.8815	High Similarity	NPC5423
0.8815	High Similarity	NPC35932
0.8815	High Similarity	NPC160991
0.8815	High Similarity	NPC184447
0.8815	High Similarity	NPC16208
0.8815	High Similarity	NPC201587
0.8811	High Similarity	NPC93924
0.8811	High Similarity	NPC236166
0.8806	High Similarity	NPC472338
0.8794	High Similarity	NPC474444
0.8794	High Similarity	NPC473090
0.8794	High Similarity	NPC93433
0.8794	High Similarity	NPC284881
0.8794	High Similarity	NPC264706
0.8786	High Similarity	NPC145319
0.8786	High Similarity	NPC131971
0.8779	High Similarity	NPC20443
0.8779	High Similarity	NPC146886
0.8779	High Similarity	NPC60517
0.8777	High Similarity	NPC288452
0.8777	High Similarity	NPC106944
0.8777	High Similarity	NPC289690
0.8769	High Similarity	NPC71090
0.8768	High Similarity	NPC281780
0.8768	High Similarity	NPC260425
0.8767	High Similarity	NPC150442
0.8759	High Similarity	NPC164787
0.8759	High Similarity	NPC470356
0.8759	High Similarity	NPC94750
0.8759	High Similarity	NPC476870
0.8759	High Similarity	NPC260898
0.8759	High Similarity	NPC112246
0.8759	High Similarity	NPC474206
0.8759	High Similarity	NPC61946
0.8759	High Similarity	NPC112939
0.8759	High Similarity	NPC121812
0.8759	High Similarity	NPC234333
0.8759	High Similarity	NPC47398
0.875	High Similarity	NPC111785
0.875	High Similarity	NPC478242
0.8741	High Similarity	NPC178129
0.8741	High Similarity	NPC309787
0.8741	High Similarity	NPC41844
0.8731	High Similarity	NPC285339
0.8731	High Similarity	NPC222004
0.8731	High Similarity	NPC190629
0.8731	High Similarity	NPC3439
0.8731	High Similarity	NPC210623
0.8731	High Similarity	NPC273295
0.8731	High Similarity	NPC226788
0.8731	High Similarity	NPC470258
0.8731	High Similarity	NPC218856
0.8731	High Similarity	NPC241354
0.8731	High Similarity	NPC202582
0.8731	High Similarity	NPC48315
0.8723	High Similarity	NPC91492
0.8723	High Similarity	NPC34245
0.8723	High Similarity	NPC7439
0.8723	High Similarity	NPC256555

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 NPC471665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	847
0.2-0.3	1809
0.3-0.4	2625
0.4-0.5	1771
0.5-0.6	966
0.6-0.7	678
0.7-0.8	162
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD7266	Discontinued
0.8676	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1612	Clinical (unspecified phase)
0.8621	High Similarity	NPD1653	Approved
0.8593	High Similarity	NPD3027	Phase 3
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD6190	Approved
0.8146	Intermediate Similarity	NPD1934	Approved
0.8014	Intermediate Similarity	NPD4628	Phase 3
0.7974	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD4340	Discontinued
0.7914	Intermediate Similarity	NPD2861	Phase 2
0.7887	Intermediate Similarity	NPD4060	Phase 1
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD6166	Phase 2
0.7862	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2801	Approved
0.7853	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD228	Approved
0.784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7054	Approved
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7823	Intermediate Similarity	NPD1652	Phase 2
0.7817	Intermediate Similarity	NPD6233	Phase 2
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD7472	Approved
0.7761	Intermediate Similarity	NPD5536	Phase 2
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7742	Intermediate Similarity	NPD1465	Phase 2
0.7737	Intermediate Similarity	NPD1091	Approved
0.7733	Intermediate Similarity	NPD1511	Approved
0.7683	Intermediate Similarity	NPD7685	Pre-registration
0.7676	Intermediate Similarity	NPD7095	Approved
0.7664	Intermediate Similarity	NPD3496	Discontinued
0.7658	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD3686	Approved
0.7647	Intermediate Similarity	NPD3687	Approved
0.7639	Intermediate Similarity	NPD1558	Phase 1
0.7632	Intermediate Similarity	NPD1512	Approved
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7622	Intermediate Similarity	NPD6798	Discontinued
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7609	Intermediate Similarity	NPD1610	Phase 2
0.7606	Intermediate Similarity	NPD4908	Phase 1
0.7603	Intermediate Similarity	NPD4536	Approved
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7595	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7075	Discontinued
0.7594	Intermediate Similarity	NPD5283	Phase 1
0.7586	Intermediate Similarity	NPD5124	Phase 1
0.7586	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD230	Phase 1
0.7584	Intermediate Similarity	NPD6674	Discontinued
0.7584	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5402	Approved
0.7576	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD1548	Phase 1
0.7564	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD8127	Discontinued
0.7551	Intermediate Similarity	NPD5588	Approved
0.7551	Intermediate Similarity	NPD5960	Phase 3
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD7228	Approved
0.7538	Intermediate Similarity	NPD1358	Approved
0.7534	Intermediate Similarity	NPD6653	Approved
0.7533	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4110	Phase 3
0.7532	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD4966	Approved
0.7532	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD7808	Phase 3
0.7519	Intermediate Similarity	NPD5535	Approved
0.7517	Intermediate Similarity	NPD3620	Phase 2
0.7517	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3705	Approved
0.7481	Intermediate Similarity	NPD2684	Approved
0.747	Intermediate Similarity	NPD7038	Approved
0.747	Intermediate Similarity	NPD7039	Approved
0.7468	Intermediate Similarity	NPD5403	Approved
0.7467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD447	Suspended
0.7466	Intermediate Similarity	NPD6355	Discontinued
0.7453	Intermediate Similarity	NPD7199	Phase 2
0.7451	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5763	Approved
0.745	Intermediate Similarity	NPD5762	Approved
0.7448	Intermediate Similarity	NPD4062	Phase 3
0.7447	Intermediate Similarity	NPD3225	Approved
0.7434	Intermediate Similarity	NPD5058	Phase 3
0.7432	Intermediate Similarity	NPD7033	Discontinued
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7417	Intermediate Similarity	NPD3750	Approved
0.7413	Intermediate Similarity	NPD9494	Approved
0.7405	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1549	Phase 2
0.7397	Intermediate Similarity	NPD4140	Approved
0.7391	Intermediate Similarity	NPD1357	Approved
0.7388	Intermediate Similarity	NPD7843	Approved
0.7386	Intermediate Similarity	NPD6799	Approved
0.7383	Intermediate Similarity	NPD2935	Discontinued
0.7376	Intermediate Similarity	NPD2982	Phase 2
0.7376	Intermediate Similarity	NPD2983	Phase 2
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD7097	Phase 1
0.7357	Intermediate Similarity	NPD1535	Discovery
0.7355	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7157	Approved
0.7351	Intermediate Similarity	NPD3060	Approved
0.7347	Intermediate Similarity	NPD1933	Approved
0.7342	Intermediate Similarity	NPD6801	Discontinued
0.7338	Intermediate Similarity	NPD5401	Approved
0.7338	Intermediate Similarity	NPD3536	Discontinued
0.7338	Intermediate Similarity	NPD5846	Approved
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3134	Approved
0.7328	Intermediate Similarity	NPD968	Approved
0.7319	Intermediate Similarity	NPD1894	Discontinued
0.7305	Intermediate Similarity	NPD1481	Phase 2
0.7305	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD2981	Phase 2
0.7303	Intermediate Similarity	NPD8166	Discontinued
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7293	Intermediate Similarity	NPD3022	Approved
0.7293	Intermediate Similarity	NPD3021	Approved
0.7292	Intermediate Similarity	NPD3018	Phase 2
0.7285	Intermediate Similarity	NPD2424	Discontinued
0.7284	Intermediate Similarity	NPD5494	Approved
0.7278	Intermediate Similarity	NPD6385	Approved
0.7278	Intermediate Similarity	NPD6386	Approved
0.7273	Intermediate Similarity	NPD290	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD6032	Approved
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7266	Intermediate Similarity	NPD5585	Approved
0.7261	Intermediate Similarity	NPD3455	Phase 2
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4237	Approved
0.7237	Intermediate Similarity	NPD4162	Approved
0.7237	Intermediate Similarity	NPD4236	Phase 3
0.7229	Intermediate Similarity	NPD3751	Discontinued
0.7226	Intermediate Similarity	NPD6671	Approved
0.7226	Intermediate Similarity	NPD4123	Phase 3
0.7222	Intermediate Similarity	NPD6584	Phase 3
0.7214	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD1778	Approved
0.7203	Intermediate Similarity	NPD8651	Approved
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.7188	Intermediate Similarity	NPD2977	Approved
0.7188	Intermediate Similarity	NPD2978	Approved
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7179	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8312	Approved
0.7176	Intermediate Similarity	NPD8313	Approved
0.717	Intermediate Similarity	NPD7411	Suspended
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7168	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD291	Approved
0.7153	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4749	Approved
0.7124	Intermediate Similarity	NPD5177	Phase 3
0.7123	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5735	Approved
0.7107	Intermediate Similarity	NPD4678	Approved
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7107	Intermediate Similarity	NPD4675	Approved
0.7105	Intermediate Similarity	NPD1375	Discontinued
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7097	Intermediate Similarity	NPD7440	Discontinued
0.7095	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD17	Approved
0.7091	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD1510	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