NPASS Compound

Structure

NPC126206 OpenBabel07101719242D 26 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 3.4641 -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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -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 -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 0.8660 -0.5000 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 0.8660 -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 2 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -4.5000 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 -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 24 1 0 0 0 0 2 6 2 0 0 0 0 2 11 1 0 0 0 0 3 7 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 14 1 0 0 0 0 7 18 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 15 1 0 0 0 0 10 20 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 12 1 1 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	2.08
LogD:	1.789
LogS:	-4.11
# Rotatable Bonds:	5
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	3.184
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.349
MDCK Permeability:	6.416323685698444e-06
Pgp-inhibitor:	0.112
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.591

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	92.86897277832031%
Volume Distribution (VD):	0.287
Pgp-substrate:	3.3883109092712402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	2.361
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.697
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.281
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.075
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC126206

Natural Product ID:	NPC126206
*Common Name:**	Arteminorin D
IUPAC Name:	(E)-3-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	MDAPOPYYLXOSPU-GHAAFOEMSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-24-15-9-12(4-5-13(15)21)19-17(10-20)25-16-8-11(3-7-18(22)23)2-6-14(16)26-19/h2-9,17,19-21H,10H2,1H3,(H,22,23)/b7-3+/t17-,19-/m1/s1
SMILES:	OC[C@H]1Oc2cc(/C=C/C(=O)O)ccc2O[C@@H]1c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3088129
PubChem CID:	44178673
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[524226]

☑ 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 NPC126206 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	300
0.1-0.2	1391
0.2-0.3	3934
0.3-0.4	9582
0.4-0.5	8724
0.5-0.6	3633
0.6-0.7	7356
0.7-0.8	6217
0.8-0.85	1173
0.85-0.9	321
0.9-0.95	60
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC471665
0.9923	High Similarity	NPC471664
0.9618	High Similarity	NPC135127
0.9545	High Similarity	NPC214729
0.9485	High Similarity	NPC478239
0.947	High Similarity	NPC237594
0.947	High Similarity	NPC249791
0.947	High Similarity	NPC476387
0.947	High Similarity	NPC119060
0.9412	High Similarity	NPC157816
0.9412	High Similarity	NPC140502
0.9385	High Similarity	NPC5851
0.9385	High Similarity	NPC86030
0.9353	High Similarity	NPC476347
0.9348	High Similarity	NPC274960
0.9348	High Similarity	NPC473909
0.9348	High Similarity	NPC143120
0.9338	High Similarity	NPC186406
0.9338	High Similarity	NPC83375
0.9338	High Similarity	NPC224876
0.9308	High Similarity	NPC72529
0.9286	High Similarity	NPC187398
0.9286	High Similarity	NPC476348
0.9281	High Similarity	NPC199928
0.9275	High Similarity	NPC232228
0.927	High Similarity	NPC278469
0.927	High Similarity	NPC193722
0.9231	High Similarity	NPC41706
0.9231	High Similarity	NPC292056
0.9231	High Similarity	NPC118787
0.9231	High Similarity	NPC147821
0.9231	High Similarity	NPC111247
0.9231	High Similarity	NPC183181
0.9231	High Similarity	NPC319625
0.9231	High Similarity	NPC163332
0.922	High Similarity	NPC98809
0.922	High Similarity	NPC476394
0.922	High Similarity	NPC106138
0.9209	High Similarity	NPC34587
0.9209	High Similarity	NPC476382
0.9209	High Similarity	NPC100998
0.9209	High Similarity	NPC252292
0.9209	High Similarity	NPC163898
0.9209	High Similarity	NPC34927
0.9191	High Similarity	NPC100389
0.916	High Similarity	NPC252307
0.916	High Similarity	NPC245826
0.916	High Similarity	NPC474178
0.9155	High Similarity	NPC205727
0.9155	High Similarity	NPC21184
0.9155	High Similarity	NPC120426
0.9155	High Similarity	NPC294522
0.9154	High Similarity	NPC120225
0.9154	High Similarity	NPC213552
0.9154	High Similarity	NPC178284
0.9154	High Similarity	NPC191037
0.9154	High Similarity	NPC58607
0.9143	High Similarity	NPC476865
0.9137	High Similarity	NPC292443
0.913	High Similarity	NPC67467
0.9124	High Similarity	NPC267291
0.9124	High Similarity	NPC202700
0.9085	High Similarity	NPC475250
0.9085	High Similarity	NPC30688
0.9085	High Similarity	NPC176903
0.9078	High Similarity	NPC232992
0.9077	High Similarity	NPC289459
0.9077	High Similarity	NPC194519
0.9071	High Similarity	NPC476866
0.9071	High Similarity	NPC476869
0.9071	High Similarity	NPC476868
0.9071	High Similarity	NPC476864
0.9044	High Similarity	NPC37468
0.9044	High Similarity	NPC471719
0.9044	High Similarity	NPC157554
0.9044	High Similarity	NPC186418
0.9037	High Similarity	NPC111635
0.9037	High Similarity	NPC67247
0.9037	High Similarity	NPC170694
0.9014	High Similarity	NPC472969
0.9014	High Similarity	NPC478237
0.9007	High Similarity	NPC268515
0.9007	High Similarity	NPC40222
0.9	High Similarity	NPC110063
0.9	High Similarity	NPC48990
0.9	High Similarity	NPC246704
0.9	High Similarity	NPC94276
0.9	High Similarity	NPC109822
0.9	High Similarity	NPC114901
0.9	High Similarity	NPC476867
0.9	High Similarity	NPC293701
0.8978	High Similarity	NPC470413
0.8978	High Similarity	NPC138738
0.8958	High Similarity	NPC300329
0.8955	High Similarity	NPC472597
0.8951	High Similarity	NPC471062
0.8951	High Similarity	NPC473427
0.8951	High Similarity	NPC259347
0.8951	High Similarity	NPC306890
0.8951	High Similarity	NPC476398
0.8951	High Similarity	NPC476386
0.8951	High Similarity	NPC94871
0.8951	High Similarity	NPC470933
0.8947	High Similarity	NPC83062
0.8944	High Similarity	NPC15577
0.8936	High Similarity	NPC262182
0.8936	High Similarity	NPC287615
0.8936	High Similarity	NPC216819
0.8936	High Similarity	NPC83743
0.8923	High Similarity	NPC279379
0.8913	High Similarity	NPC226005
0.8905	High Similarity	NPC306441
0.8905	High Similarity	NPC471988
0.8905	High Similarity	NPC120852
0.8905	High Similarity	NPC16435
0.8897	High Similarity	NPC886
0.8897	High Similarity	NPC163598
0.8897	High Similarity	NPC309744
0.8897	High Similarity	NPC120774
0.8897	High Similarity	NPC34293
0.8897	High Similarity	NPC287597
0.8897	High Similarity	NPC478085
0.8897	High Similarity	NPC264875
0.8889	High Similarity	NPC5423
0.8889	High Similarity	NPC257970
0.8889	High Similarity	NPC470927
0.8889	High Similarity	NPC35932
0.8889	High Similarity	NPC201587
0.8889	High Similarity	NPC160991
0.8889	High Similarity	NPC253105
0.8889	High Similarity	NPC188393
0.8889	High Similarity	NPC470934
0.8889	High Similarity	NPC7903
0.8889	High Similarity	NPC245120
0.8889	High Similarity	NPC16208
0.8889	High Similarity	NPC184447
0.8889	High Similarity	NPC259576
0.8889	High Similarity	NPC221091
0.8881	High Similarity	NPC236166
0.8881	High Similarity	NPC472338
0.8881	High Similarity	NPC93924
0.8865	High Similarity	NPC473090
0.8865	High Similarity	NPC160378
0.8865	High Similarity	NPC284881
0.8865	High Similarity	NPC93433
0.8865	High Similarity	NPC474444
0.8865	High Similarity	NPC264706
0.8857	High Similarity	NPC131971
0.8855	High Similarity	NPC146886
0.8855	High Similarity	NPC20443
0.8855	High Similarity	NPC60517
0.8849	High Similarity	NPC289690
0.8849	High Similarity	NPC288452
0.8846	High Similarity	NPC71090
0.8841	High Similarity	NPC78363
0.8841	High Similarity	NPC281780
0.8836	High Similarity	NPC150442
0.8832	High Similarity	NPC61946
0.8832	High Similarity	NPC121812
0.8832	High Similarity	NPC260898
0.8832	High Similarity	NPC470356
0.8832	High Similarity	NPC234333
0.8832	High Similarity	NPC94750
0.8832	High Similarity	NPC47398
0.8832	High Similarity	NPC112246
0.8832	High Similarity	NPC112939
0.8832	High Similarity	NPC474206
0.8824	High Similarity	NPC36490
0.8819	High Similarity	NPC111785
0.8819	High Similarity	NPC478242
0.8811	High Similarity	NPC178129
0.8806	High Similarity	NPC222004
0.8806	High Similarity	NPC285339
0.8806	High Similarity	NPC48315
0.8806	High Similarity	NPC190629
0.8806	High Similarity	NPC470258
0.8806	High Similarity	NPC3439
0.8806	High Similarity	NPC210623
0.8806	High Similarity	NPC226788
0.8806	High Similarity	NPC218856
0.8806	High Similarity	NPC273295
0.8806	High Similarity	NPC202582
0.8797	High Similarity	NPC118533
0.8797	High Similarity	NPC165045
0.8794	High Similarity	NPC256555
0.8794	High Similarity	NPC34245
0.8794	High Similarity	NPC7439
0.8794	High Similarity	NPC110067
0.8794	High Similarity	NPC91492
0.8788	High Similarity	NPC87113
0.8786	High Similarity	NPC476385
0.8786	High Similarity	NPC134405
0.8784	High Similarity	NPC11411
0.8784	High Similarity	NPC471405
0.8779	High Similarity	NPC471693
0.8777	High Similarity	NPC197316
0.8777	High Similarity	NPC64141
0.8777	High Similarity	NPC472350
0.8777	High Similarity	NPC476383
0.8777	High Similarity	NPC68092

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 NPC126206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	840
0.2-0.3	1764
0.3-0.4	2616
0.4-0.5	1776
0.5-0.6	998
0.6-0.7	700
0.7-0.8	180
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD7266	Discontinued
0.8667	High Similarity	NPD3027	Phase 3
0.8613	High Similarity	NPD1613	Approved
0.8613	High Similarity	NPD1612	Clinical (unspecified phase)
0.8562	High Similarity	NPD1653	Approved
0.8358	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1934	Approved
0.8151	Intermediate Similarity	NPD6190	Approved
0.8082	Intermediate Similarity	NPD4628	Phase 3
0.8039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD4060	Phase 1
0.7925	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6166	Phase 2
0.7923	Intermediate Similarity	NPD228	Approved
0.7922	Intermediate Similarity	NPD2801	Approved
0.7919	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD4340	Discontinued
0.7891	Intermediate Similarity	NPD1652	Phase 2
0.7888	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD7054	Approved
0.7887	Intermediate Similarity	NPD6233	Phase 2
0.7871	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD2861	Phase 2
0.784	Intermediate Similarity	NPD7074	Phase 3
0.784	Intermediate Similarity	NPD7472	Approved
0.7836	Intermediate Similarity	NPD5536	Phase 2
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7821	Intermediate Similarity	NPD3882	Suspended
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7095	Approved
0.7744	Intermediate Similarity	NPD7685	Pre-registration
0.7737	Intermediate Similarity	NPD3496	Discontinued
0.7722	Intermediate Similarity	NPD6234	Discontinued
0.7712	Intermediate Similarity	NPD3687	Approved
0.7712	Intermediate Similarity	NPD3686	Approved
0.7708	Intermediate Similarity	NPD1558	Phase 1
0.7692	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7682	Intermediate Similarity	NPD1511	Approved
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7681	Intermediate Similarity	NPD1091	Approved
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7671	Intermediate Similarity	NPD4536	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4538	Approved
0.7669	Intermediate Similarity	NPD5283	Phase 1
0.7658	Intermediate Similarity	NPD7075	Discontinued
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6674	Discontinued
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7628	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD8127	Discontinued
0.7615	Intermediate Similarity	NPD1358	Approved
0.7607	Intermediate Similarity	NPD7228	Approved
0.7603	Intermediate Similarity	NPD6653	Approved
0.76	Intermediate Similarity	NPD4110	Phase 3
0.76	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4967	Phase 2
0.7595	Intermediate Similarity	NPD4965	Approved
0.7595	Intermediate Similarity	NPD4966	Approved
0.7594	Intermediate Similarity	NPD5535	Approved
0.759	Intermediate Similarity	NPD7808	Phase 3
0.7586	Intermediate Similarity	NPD3620	Phase 2
0.7586	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1512	Approved
0.758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7554	Intermediate Similarity	NPD3705	Approved
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6355	Discontinued
0.7534	Intermediate Similarity	NPD447	Suspended
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5402	Approved
0.753	Intermediate Similarity	NPD7038	Approved
0.753	Intermediate Similarity	NPD7039	Approved
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD5763	Approved
0.7517	Intermediate Similarity	NPD4062	Phase 3
0.7516	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD5058	Phase 3
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7483	Intermediate Similarity	NPD9494	Approved
0.7468	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4140	Approved
0.7464	Intermediate Similarity	NPD1357	Approved
0.7463	Intermediate Similarity	NPD7843	Approved
0.7451	Intermediate Similarity	NPD6799	Approved
0.745	Intermediate Similarity	NPD2935	Discontinued
0.7447	Intermediate Similarity	NPD2982	Phase 2
0.7447	Intermediate Similarity	NPD2983	Phase 2
0.7432	Intermediate Similarity	NPD7097	Phase 1
0.7426	Intermediate Similarity	NPD7157	Approved
0.7425	Intermediate Similarity	NPD6559	Discontinued
0.7419	Intermediate Similarity	NPD5403	Approved
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3060	Approved
0.7415	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD3134	Approved
0.7405	Intermediate Similarity	NPD6801	Discontinued
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3536	Discontinued
0.7394	Intermediate Similarity	NPD3225	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7376	Intermediate Similarity	NPD2981	Phase 2
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3750	Approved
0.7368	Intermediate Similarity	NPD8166	Discontinued
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD8455	Phase 2
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7351	Intermediate Similarity	NPD2424	Discontinued
0.7348	Intermediate Similarity	NPD290	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD2797	Approved
0.7342	Intermediate Similarity	NPD6385	Approved
0.7342	Intermediate Similarity	NPD6386	Approved
0.7338	Intermediate Similarity	NPD4357	Discontinued
0.7338	Intermediate Similarity	NPD5585	Approved
0.7333	Intermediate Similarity	NPD6032	Approved
0.7325	Intermediate Similarity	NPD3455	Phase 2
0.7317	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1535	Discovery
0.7303	Intermediate Similarity	NPD4237	Approved
0.7303	Intermediate Similarity	NPD4236	Phase 3
0.7303	Intermediate Similarity	NPD4162	Approved
0.7299	Intermediate Similarity	NPD6671	Approved
0.7292	Intermediate Similarity	NPD6584	Phase 3
0.729	Intermediate Similarity	NPD4123	Phase 3
0.729	Intermediate Similarity	NPD5401	Approved
0.7286	Intermediate Similarity	NPD6516	Phase 2
0.7286	Intermediate Similarity	NPD4626	Approved
0.7286	Intermediate Similarity	NPD5846	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD968	Approved
0.7273	Intermediate Similarity	NPD8651	Approved
0.7266	Intermediate Similarity	NPD1894	Discontinued
0.726	Intermediate Similarity	NPD4625	Phase 3
0.7254	Intermediate Similarity	NPD1481	Phase 2
0.725	Intermediate Similarity	NPD2978	Approved
0.725	Intermediate Similarity	NPD2977	Approved
0.7244	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7411	Suspended
0.7231	Intermediate Similarity	NPD291	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7215	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5691	Approved
0.7211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD2677	Approved
0.7203	Intermediate Similarity	NPD4749	Approved
0.7192	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5177	Phase 3
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1375	Discontinued
0.717	Intermediate Similarity	NPD4678	Approved
0.717	Intermediate Similarity	NPD4675	Approved
0.717	Intermediate Similarity	NPD6599	Discontinued
0.7163	Intermediate Similarity	NPD17	Approved
0.7162	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD5772	Approved
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5773	Approved
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7135	Intermediate Similarity	NPD8313	Approved
0.7135	Intermediate Similarity	NPD8312	Approved
0.7134	Intermediate Similarity	NPD4666	Phase 3

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