NPASS Compound

Structure

NPC237440 OpenBabel07101719142D 21 23 0 0 1 0 0 0 0 0999 V2000 0.7071 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 3.4641 0.0000 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 -0.8660 1.5000 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 1.7321 1.0000 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 0.0000 3.0000 0.0000 C 0 0 1 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 -0.8660 2.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 1 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 6 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 1 1 6 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.09
Volume:	281.886
LogP:	0.745
LogD:	1.191
LogS:	-2.809
# Rotatable Bonds:	1
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.237
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.736
MDCK Permeability:	6.765313628420699e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	68.56782531738281%
Volume Distribution (VD):	0.304
Pgp-substrate:	42.927879333496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.446
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	6.767
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.466
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC237440

Natural Product ID:	NPC237440
*Common Name:**	Altenuene
IUPAC Name:	(2S,3S,4aS)-2,3,7-trihydroxy-9-methoxy-4a-methyl-3,4-dihydro-2H-benzo[c]chromen-6-one
Synonyms:	Altenuene
Standard InCHIKey:	MMHTXEATDNFMMY-WBIUFABUSA-N
Standard InCHI:	InChI=1S/C15H16O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,10,12,16-18H,6H2,1-2H3/t10-,12-,15-/m0/s1
SMILES:	COc1cc(O)c2c(c1)C1=C[C@H](O)[C@H](C[C@@]1(OC2=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482228
PubChem CID:	34687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32670	tubeufiaceae	Family	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643037]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	18.0	mm	PMID[497493]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	20.0	mm	PMID[497493]

☑ 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 NPC237440 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	337
0.1-0.2	1402
0.2-0.3	3281
0.3-0.4	7230
0.4-0.5	10957
0.5-0.6	4012
0.6-0.7	5217
0.7-0.8	7308
0.8-0.85	2389
0.85-0.9	464
0.9-0.95	88
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC270160
0.9658	High Similarity	NPC167903
0.9577	High Similarity	NPC469542
0.9456	High Similarity	NPC70016
0.9456	High Similarity	NPC215921
0.9452	High Similarity	NPC77325
0.9452	High Similarity	NPC4423
0.9441	High Similarity	NPC51106
0.9375	High Similarity	NPC280404
0.9375	High Similarity	NPC86373
0.9375	High Similarity	NPC277426
0.9375	High Similarity	NPC210425
0.9371	High Similarity	NPC469579
0.9329	High Similarity	NPC281477
0.9301	High Similarity	NPC1704
0.9301	High Similarity	NPC67650
0.9272	High Similarity	NPC246466
0.9267	High Similarity	NPC82592
0.9267	High Similarity	NPC16082
0.9257	High Similarity	NPC469619
0.9257	High Similarity	NPC179178
0.9257	High Similarity	NPC469670
0.9247	High Similarity	NPC260946
0.9247	High Similarity	NPC473023
0.9236	High Similarity	NPC474385
0.9211	High Similarity	NPC470339
0.9205	High Similarity	NPC472050
0.92	High Similarity	NPC192189
0.9195	High Similarity	NPC240768
0.9195	High Similarity	NPC200773
0.9184	High Similarity	NPC210320
0.9172	High Similarity	NPC472006
0.9167	High Similarity	NPC53649
0.9161	High Similarity	NPC32360
0.9155	High Similarity	NPC135837
0.915	High Similarity	NPC472055
0.9145	High Similarity	NPC77679
0.9145	High Similarity	NPC84935
0.9145	High Similarity	NPC190020
0.9139	High Similarity	NPC199926
0.9133	High Similarity	NPC470340
0.9122	High Similarity	NPC73411
0.9122	High Similarity	NPC215711
0.9116	High Similarity	NPC107625
0.9097	High Similarity	NPC158472
0.9091	High Similarity	NPC94248
0.9091	High Similarity	NPC472602
0.9091	High Similarity	NPC212693
0.9085	High Similarity	NPC235115
0.9079	High Similarity	NPC227062
0.9079	High Similarity	NPC150227
0.9073	High Similarity	NPC155686
0.9073	High Similarity	NPC472799
0.9067	High Similarity	NPC132990
0.9067	High Similarity	NPC46882
0.9054	High Similarity	NPC472036
0.9048	High Similarity	NPC83272
0.9034	High Similarity	NPC472604
0.9034	High Similarity	NPC158634
0.9034	High Similarity	NPC475730
0.9034	High Similarity	NPC472605
0.9034	High Similarity	NPC90411
0.9028	High Similarity	NPC139634
0.9028	High Similarity	NPC105456
0.9028	High Similarity	NPC268052
0.9028	High Similarity	NPC247409
0.9021	High Similarity	NPC70380
0.9014	High Similarity	NPC180905
0.9014	High Similarity	NPC182496
0.9013	High Similarity	NPC99381
0.9013	High Similarity	NPC170189
0.9013	High Similarity	NPC208173
0.9013	High Similarity	NPC69043
0.9013	High Similarity	NPC478230
0.9007	High Similarity	NPC470338
0.9007	High Similarity	NPC51824
0.9007	High Similarity	NPC478224
0.9007	High Similarity	NPC115249
0.9007	High Similarity	NPC268992
0.9007	High Similarity	NPC113608
0.9007	High Similarity	NPC256141
0.9007	High Similarity	NPC470337
0.9007	High Similarity	NPC184284
0.9007	High Similarity	NPC76041
0.9	High Similarity	NPC150928
0.9	High Similarity	NPC472891
0.8993	High Similarity	NPC471641
0.8993	High Similarity	NPC471642
0.8993	High Similarity	NPC153417
0.8993	High Similarity	NPC240253
0.8993	High Similarity	NPC240622
0.8986	High Similarity	NPC267509
0.8973	High Similarity	NPC82913
0.8973	High Similarity	NPC250755
0.8973	High Similarity	NPC322112
0.8968	High Similarity	NPC117985
0.8966	High Similarity	NPC472601
0.8966	High Similarity	NPC472600
0.8966	High Similarity	NPC155205
0.8958	High Similarity	NPC191835
0.8954	High Similarity	NPC24640
0.8947	High Similarity	NPC291510
0.8947	High Similarity	NPC137301
0.8947	High Similarity	NPC116850
0.8947	High Similarity	NPC197188
0.8947	High Similarity	NPC144801
0.8947	High Similarity	NPC478231
0.8947	High Similarity	NPC43872
0.8947	High Similarity	NPC238672
0.894	High Similarity	NPC204350
0.8933	High Similarity	NPC476684
0.8926	High Similarity	NPC85773
0.8926	High Similarity	NPC476463
0.8919	High Similarity	NPC472034
0.8919	High Similarity	NPC32470
0.8919	High Similarity	NPC473692
0.8919	High Similarity	NPC134621
0.8917	High Similarity	NPC7752
0.8912	High Similarity	NPC159721
0.8912	High Similarity	NPC471731
0.8904	High Similarity	NPC472603
0.8904	High Similarity	NPC244923
0.8897	High Similarity	NPC88269
0.8896	High Similarity	NPC472889
0.8896	High Similarity	NPC473395
0.8889	High Similarity	NPC67396
0.8889	High Similarity	NPC175192
0.8889	High Similarity	NPC79998
0.8889	High Similarity	NPC472890
0.8889	High Similarity	NPC68727
0.8889	High Similarity	NPC478221
0.8882	High Similarity	NPC474843
0.8882	High Similarity	NPC180944
0.8882	High Similarity	NPC273483
0.8882	High Similarity	NPC217447
0.8882	High Similarity	NPC295646
0.8881	High Similarity	NPC142027
0.8874	High Similarity	NPC470107
0.8874	High Similarity	NPC180351
0.8874	High Similarity	NPC475460
0.8874	High Similarity	NPC96501
0.8873	High Similarity	NPC153783
0.8861	High Similarity	NPC20237
0.8859	High Similarity	NPC472033
0.8859	High Similarity	NPC138978
0.8859	High Similarity	NPC237208
0.8854	High Similarity	NPC249181
0.8851	High Similarity	NPC66404
0.8851	High Similarity	NPC42540
0.8851	High Similarity	NPC95123
0.8851	High Similarity	NPC151607
0.8851	High Similarity	NPC95751
0.8844	High Similarity	NPC471733
0.8839	High Similarity	NPC329091
0.8836	High Similarity	NPC165172
0.8836	High Similarity	NPC64664
0.8836	High Similarity	NPC469523
0.8831	High Similarity	NPC164427
0.8828	High Similarity	NPC126739
0.8828	High Similarity	NPC197666
0.8828	High Similarity	NPC478200
0.8828	High Similarity	NPC33144
0.8824	High Similarity	NPC301233
0.8824	High Similarity	NPC471695
0.8816	High Similarity	NPC228662
0.8811	High Similarity	NPC175943
0.8805	High Similarity	NPC283041
0.8805	High Similarity	NPC249977
0.88	High Similarity	NPC8817
0.88	High Similarity	NPC21835
0.88	High Similarity	NPC14098
0.88	High Similarity	NPC91902
0.88	High Similarity	NPC166583
0.88	High Similarity	NPC47388
0.88	High Similarity	NPC470670
0.88	High Similarity	NPC53362
0.88	High Similarity	NPC473133
0.88	High Similarity	NPC81835
0.8797	High Similarity	NPC191930
0.8792	High Similarity	NPC312789
0.8792	High Similarity	NPC316535
0.8792	High Similarity	NPC29577
0.879	High Similarity	NPC472964
0.8784	High Similarity	NPC472610
0.8784	High Similarity	NPC478202
0.8784	High Similarity	NPC73028
0.8784	High Similarity	NPC471639
0.8784	High Similarity	NPC471643
0.8784	High Similarity	NPC310340
0.8782	High Similarity	NPC472902
0.8782	High Similarity	NPC321399
0.8782	High Similarity	NPC24627
0.8776	High Similarity	NPC220106
0.8776	High Similarity	NPC182421
0.8776	High Similarity	NPC275734
0.8776	High Similarity	NPC313123
0.8776	High Similarity	NPC478217
0.8774	High Similarity	NPC478226
0.8774	High Similarity	NPC478225
0.8766	High Similarity	NPC20541

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 NPC237440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	905
0.2-0.3	1795
0.3-0.4	2521
0.4-0.5	1874
0.5-0.6	1101
0.6-0.7	466
0.7-0.8	169
0.8-0.85	29
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD970	Clinical (unspecified phase)
0.8667	High Similarity	NPD2533	Approved
0.8667	High Similarity	NPD2532	Approved
0.8667	High Similarity	NPD2534	Approved
0.8581	High Similarity	NPD2393	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD4380	Phase 2
0.8446	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8389	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8311	Intermediate Similarity	NPD1510	Phase 2
0.8302	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6959	Discontinued
0.8235	Intermediate Similarity	NPD1511	Approved
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8165	Intermediate Similarity	NPD6801	Discontinued
0.8163	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8129	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD6799	Approved
0.8113	Intermediate Similarity	NPD2801	Approved
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8098	Intermediate Similarity	NPD5710	Approved
0.8098	Intermediate Similarity	NPD5711	Approved
0.8075	Intermediate Similarity	NPD3749	Approved
0.8072	Intermediate Similarity	NPD7054	Approved
0.8063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8024	Intermediate Similarity	NPD7472	Approved
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6797	Phase 2
0.7964	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5402	Approved
0.7931	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7251	Discontinued
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4628	Phase 3
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7901	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7892	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7808	Phase 3
0.787	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2800	Approved
0.7848	Intermediate Similarity	NPD5403	Approved
0.7834	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3748	Approved
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7758	Intermediate Similarity	NPD5494	Approved
0.7722	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD37	Approved
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1243	Approved
0.7625	Intermediate Similarity	NPD920	Approved
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD8150	Discontinued
0.7597	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7033	Discontinued
0.7588	Intermediate Similarity	NPD7228	Approved
0.7566	Intermediate Similarity	NPD943	Approved
0.7566	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1613	Approved
0.756	Intermediate Similarity	NPD3787	Discontinued
0.7547	Intermediate Similarity	NPD7390	Discontinued
0.7531	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7516	Intermediate Similarity	NPD1652	Phase 2
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD9545	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9717	Approved
0.7469	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD1203	Approved
0.7434	Intermediate Similarity	NPD3764	Approved
0.7434	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD6777	Approved
0.7432	Intermediate Similarity	NPD6780	Approved
0.7432	Intermediate Similarity	NPD6781	Approved
0.7432	Intermediate Similarity	NPD6776	Approved
0.7432	Intermediate Similarity	NPD4749	Approved
0.7432	Intermediate Similarity	NPD6782	Approved
0.7432	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6190	Approved
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7372	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD9269	Phase 2
0.7361	Intermediate Similarity	NPD9493	Approved
0.7356	Intermediate Similarity	NPD5953	Discontinued
0.7353	Intermediate Similarity	NPD7229	Phase 3
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7286	Phase 2
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD5408	Approved
0.7325	Intermediate Similarity	NPD5405	Approved
0.7325	Intermediate Similarity	NPD5404	Approved
0.732	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD411	Approved
0.7316	Intermediate Similarity	NPD7783	Phase 2
0.7316	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.7305	Intermediate Similarity	NPD4288	Approved
0.7305	Intermediate Similarity	NPD5353	Approved
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6832	Phase 2
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7874	Approved
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7239	Intermediate Similarity	NPD6273	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7219	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD7698	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.7219	Intermediate Similarity	NPD7697	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD9268	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1247	Approved
0.7188	Intermediate Similarity	NPD2654	Approved
0.7181	Intermediate Similarity	NPD7871	Phase 2
0.7181	Intermediate Similarity	NPD7870	Phase 2
0.7181	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.7171	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD2344	Approved
0.7166	Intermediate Similarity	NPD6823	Phase 2
0.7162	Intermediate Similarity	NPD17	Approved
0.7162	Intermediate Similarity	NPD4626	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7158	Intermediate Similarity	NPD7701	Phase 2
0.7158	Intermediate Similarity	NPD6535	Approved
0.7152	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7127	Intermediate Similarity	NPD4287	Approved
0.7124	Intermediate Similarity	NPD9494	Approved
0.7113	Intermediate Similarity	NPD7930	Approved
0.711	Intermediate Similarity	NPD5242	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