NPASS Compound

Structure

NPC150215 OpenBabel07101719512D 27 30 0 0 1 0 0 0 0 0999 V2000 4.3776 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 3.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 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 14 2 0 0 0 0 2 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 22 2 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 21 2 0 0 0 0 13 16 1 0 0 0 0 13 23 2 0 0 0 0 15 3 1 1 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 14 1 6 0 0 0 18 19 1 0 0 0 0 19 24 1 1 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.19
Volume:	394.713
LogP:	6.881
LogD:	4.376
LogS:	-4.483
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	3.591
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.83
MDCK Permeability:	1.4920235116733238e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	99.24150085449219%
Volume Distribution (VD):	3.249
Pgp-substrate:	1.2715128660202026%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.8
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.673
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	8.113
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.254
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.426
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.955
Carcinogencity:	0.402
Eye Corrosion:	0.004
Eye Irritation:	0.885
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC150215

Natural Product ID:	NPC150215
*Common Name:**	Machaeridiol C
IUPAC Name:	5-(1-benzofuran-2-yl)-2-[(1S,2S,5S)-5-methyl-2-prop-1-en-2-ylcyclohexyl]benzene-1,3-diol
Synonyms:	Machaeridiol C
Standard InCHIKey:	UPLNMKNMLLBKKI-IPELMVKDSA-N
Standard InCHI:	InChI=1S/C24H26O3/c1-14(2)18-9-8-15(3)10-19(18)24-20(25)11-17(12-21(24)26)23-13-16-6-4-5-7-22(16)27-23/h4-7,11-13,15,18-19,25-26H,1,8-10H2,2-3H3/t15-,18+,19-/m0/s1
SMILES:	C=C(C)[C@H]1CC[C@H](C)C[C@@H]1c1c(cc(cc1O)c1cc2ccccc2o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466161
PubChem CID:	10882982
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO33402	machaerium multiflorum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[11678659]
NPO33402	machaerium multiflorum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12828466]

☑ 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	8
MIC	3
Others	5

Activity Type	# Activity
Organism	14
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[550251]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	25.0	ug.mL-1	PMID[550251]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	10.0	ug.mL-1	PMID[550251]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	12.5	ug ml-1	PMID[550251]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	45.0	ug.mL-1	PMID[550251]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	25.0	ug.mL-1	PMID[550251]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3.0	ug.mL-1	PMID[550251]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3.5	ug.mL-1	PMID[550251]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	10.0	ug.mL-1	PMID[550251]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.3	ug.mL-1	PMID[550251]
NPT2	Others	Unspecified		Ratio IC50	>	1.4	n.a.	PMID[550251]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.5	ug.mL-1	PMID[550251]
NPT2	Others	Unspecified		Ratio IC50	>	1.9	n.a.	PMID[550251]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3.0	ug.mL-1	PMID[550251]

☑ 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 NPC150215 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	402
0.1-0.2	1541
0.2-0.3	3187
0.3-0.4	8694
0.4-0.5	10340
0.5-0.6	3743
0.6-0.7	6255
0.7-0.8	7557
0.8-0.85	915
0.85-0.9	58
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC149085
0.9429	High Similarity	NPC112757
0.9384	High Similarity	NPC13282
0.9333	High Similarity	NPC226287
0.9013	High Similarity	NPC246647
0.9013	High Similarity	NPC96342
0.9013	High Similarity	NPC212967
0.9013	High Similarity	NPC164110
0.8993	High Similarity	NPC167576
0.8968	High Similarity	NPC159508
0.8947	High Similarity	NPC137100
0.8947	High Similarity	NPC180924
0.894	High Similarity	NPC72370
0.894	High Similarity	NPC235333
0.8933	High Similarity	NPC193976
0.8933	High Similarity	NPC23668
0.891	High Similarity	NPC169471
0.8889	High Similarity	NPC268360
0.8882	High Similarity	NPC213936
0.8882	High Similarity	NPC297531
0.8882	High Similarity	NPC99199
0.8882	High Similarity	NPC148938
0.8874	High Similarity	NPC142308
0.8874	High Similarity	NPC207624
0.8867	High Similarity	NPC78335
0.8867	High Similarity	NPC230713
0.8816	High Similarity	NPC472462
0.8808	High Similarity	NPC115324
0.8808	High Similarity	NPC106372
0.8808	High Similarity	NPC170169
0.8808	High Similarity	NPC58668
0.88	High Similarity	NPC178202
0.8797	High Similarity	NPC253730
0.8797	High Similarity	NPC286230
0.8792	High Similarity	NPC17101
0.8792	High Similarity	NPC77903
0.8784	High Similarity	NPC98926
0.871	High Similarity	NPC472877
0.8693	High Similarity	NPC1477
0.8693	High Similarity	NPC213608
0.8675	High Similarity	NPC226644
0.8675	High Similarity	NPC37226
0.8667	High Similarity	NPC17816
0.8658	High Similarity	NPC155144
0.8649	High Similarity	NPC1534
0.8636	High Similarity	NPC198490
0.8627	High Similarity	NPC5871
0.8609	High Similarity	NPC272194
0.8609	High Similarity	NPC135325
0.86	High Similarity	NPC210826
0.86	High Similarity	NPC300267
0.86	High Similarity	NPC51641
0.8591	High Similarity	NPC225884
0.859	High Similarity	NPC40583
0.858	High Similarity	NPC59491
0.858	High Similarity	NPC24748
0.8571	High Similarity	NPC42458
0.8571	High Similarity	NPC158261
0.8571	High Similarity	NPC183874
0.8562	High Similarity	NPC62735
0.8562	High Similarity	NPC258249
0.8553	High Similarity	NPC221868
0.8553	High Similarity	NPC37208
0.8553	High Similarity	NPC70764
0.8553	High Similarity	NPC474591
0.8544	High Similarity	NPC3448
0.8544	High Similarity	NPC477239
0.8543	High Similarity	NPC130581
0.8543	High Similarity	NPC12148
0.8543	High Similarity	NPC71055
0.8533	High Similarity	NPC230943
0.8526	High Similarity	NPC65504
0.8526	High Similarity	NPC158542
0.8506	High Similarity	NPC40356
0.8506	High Similarity	NPC154683
0.8477	Intermediate Similarity	NPC469758
0.8476	Intermediate Similarity	NPC101991
0.8471	Intermediate Similarity	NPC244750
0.8467	Intermediate Similarity	NPC302181
0.8466	Intermediate Similarity	NPC65885
0.8462	Intermediate Similarity	NPC247677
0.8462	Intermediate Similarity	NPC160015
0.8457	Intermediate Similarity	NPC476641
0.8452	Intermediate Similarity	NPC135522
0.8452	Intermediate Similarity	NPC329844
0.8447	Intermediate Similarity	NPC50394
0.8446	Intermediate Similarity	NPC473499
0.8442	Intermediate Similarity	NPC474417
0.8442	Intermediate Similarity	NPC39819
0.8442	Intermediate Similarity	NPC149526
0.8438	Intermediate Similarity	NPC136641
0.8431	Intermediate Similarity	NPC288036
0.8431	Intermediate Similarity	NPC10027
0.8431	Intermediate Similarity	NPC65775
0.8431	Intermediate Similarity	NPC329933
0.8431	Intermediate Similarity	NPC65589
0.8431	Intermediate Similarity	NPC97029
0.8431	Intermediate Similarity	NPC100985
0.8431	Intermediate Similarity	NPC39929
0.8431	Intermediate Similarity	NPC97028
0.8431	Intermediate Similarity	NPC296030
0.8431	Intermediate Similarity	NPC158338
0.8425	Intermediate Similarity	NPC163029
0.8418	Intermediate Similarity	NPC470810
0.8418	Intermediate Similarity	NPC115432
0.8418	Intermediate Similarity	NPC260296
0.8415	Intermediate Similarity	NPC300657
0.8411	Intermediate Similarity	NPC469764
0.8408	Intermediate Similarity	NPC260902
0.8408	Intermediate Similarity	NPC296957
0.84	Intermediate Similarity	NPC3732
0.84	Intermediate Similarity	NPC158871
0.84	Intermediate Similarity	NPC53192
0.8397	Intermediate Similarity	NPC226656
0.8397	Intermediate Similarity	NPC66508
0.8389	Intermediate Similarity	NPC145673
0.8387	Intermediate Similarity	NPC67654
0.8387	Intermediate Similarity	NPC87708
0.8385	Intermediate Similarity	NPC277480
0.8385	Intermediate Similarity	NPC53640
0.8378	Intermediate Similarity	NPC18457
0.8377	Intermediate Similarity	NPC227122
0.8373	Intermediate Similarity	NPC121888
0.8366	Intermediate Similarity	NPC37135
0.8366	Intermediate Similarity	NPC5537
0.8366	Intermediate Similarity	NPC39195
0.8366	Intermediate Similarity	NPC472841
0.8366	Intermediate Similarity	NPC186397
0.8366	Intermediate Similarity	NPC256672
0.8366	Intermediate Similarity	NPC27221
0.8366	Intermediate Similarity	NPC7025
0.8365	Intermediate Similarity	NPC45124
0.8365	Intermediate Similarity	NPC74854
0.8365	Intermediate Similarity	NPC18380
0.8365	Intermediate Similarity	NPC30655
0.8364	Intermediate Similarity	NPC8127
0.8364	Intermediate Similarity	NPC49667
0.8355	Intermediate Similarity	NPC299011
0.8355	Intermediate Similarity	NPC196114
0.8354	Intermediate Similarity	NPC82217
0.8354	Intermediate Similarity	NPC186113
0.8354	Intermediate Similarity	NPC218818
0.8354	Intermediate Similarity	NPC216842
0.8354	Intermediate Similarity	NPC476350
0.8354	Intermediate Similarity	NPC476640
0.8354	Intermediate Similarity	NPC239118
0.8354	Intermediate Similarity	NPC4950
0.8354	Intermediate Similarity	NPC324736
0.8354	Intermediate Similarity	NPC476349
0.8354	Intermediate Similarity	NPC177650
0.8344	Intermediate Similarity	NPC146211
0.8344	Intermediate Similarity	NPC131866
0.8333	Intermediate Similarity	NPC122365
0.8333	Intermediate Similarity	NPC470704
0.8333	Intermediate Similarity	NPC210942
0.8333	Intermediate Similarity	NPC169990
0.8333	Intermediate Similarity	NPC214632
0.8323	Intermediate Similarity	NPC116604
0.8323	Intermediate Similarity	NPC305965
0.8323	Intermediate Similarity	NPC37183
0.8323	Intermediate Similarity	NPC230848
0.8323	Intermediate Similarity	NPC72958
0.8323	Intermediate Similarity	NPC478148
0.8323	Intermediate Similarity	NPC232645
0.8323	Intermediate Similarity	NPC156244
0.8322	Intermediate Similarity	NPC109232
0.8313	Intermediate Similarity	NPC193998
0.8313	Intermediate Similarity	NPC84515
0.8313	Intermediate Similarity	NPC312056
0.8312	Intermediate Similarity	NPC269420
0.8312	Intermediate Similarity	NPC223988
0.8312	Intermediate Similarity	NPC317492
0.8312	Intermediate Similarity	NPC80370
0.8312	Intermediate Similarity	NPC266499
0.8303	Intermediate Similarity	NPC287243
0.8303	Intermediate Similarity	NPC227906
0.8302	Intermediate Similarity	NPC186325
0.8302	Intermediate Similarity	NPC220582
0.8302	Intermediate Similarity	NPC312993
0.8302	Intermediate Similarity	NPC184326
0.8302	Intermediate Similarity	NPC304839
0.8302	Intermediate Similarity	NPC292863
0.8301	Intermediate Similarity	NPC123202
0.8301	Intermediate Similarity	NPC126767
0.8301	Intermediate Similarity	NPC312929
0.8301	Intermediate Similarity	NPC34802
0.8301	Intermediate Similarity	NPC308200
0.8301	Intermediate Similarity	NPC289042
0.8301	Intermediate Similarity	NPC56433
0.8301	Intermediate Similarity	NPC245584
0.8301	Intermediate Similarity	NPC190648
0.8301	Intermediate Similarity	NPC7943
0.8301	Intermediate Similarity	NPC118027
0.8301	Intermediate Similarity	NPC22005
0.8293	Intermediate Similarity	NPC54098
0.8293	Intermediate Similarity	NPC230619
0.8291	Intermediate Similarity	NPC44199
0.8289	Intermediate Similarity	NPC131766
0.8289	Intermediate Similarity	NPC184649
0.8289	Intermediate Similarity	NPC311144

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 NPC150215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	916
0.2-0.3	1273
0.3-0.4	2478
0.4-0.5	2227
0.5-0.6	1238
0.6-0.7	486
0.7-0.8	159
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD3749	Approved
0.8243	Intermediate Similarity	NPD6099	Approved
0.8243	Intermediate Similarity	NPD6100	Approved
0.8188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2344	Approved
0.8146	Intermediate Similarity	NPD3750	Approved
0.8146	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8077	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3226	Approved
0.8069	Intermediate Similarity	NPD4625	Phase 3
0.8067	Intermediate Similarity	NPD2346	Discontinued
0.8052	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7974	Intermediate Similarity	NPD2309	Approved
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD7819	Suspended
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD2532	Approved
0.7821	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3748	Approved
0.7793	Intermediate Similarity	NPD2797	Approved
0.7792	Intermediate Similarity	NPD7003	Approved
0.7785	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD4749	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7764	Intermediate Similarity	NPD2801	Approved
0.7763	Intermediate Similarity	NPD1551	Phase 2
0.7763	Intermediate Similarity	NPD2796	Approved
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.7756	Intermediate Similarity	NPD1511	Approved
0.775	Intermediate Similarity	NPD7411	Suspended
0.7744	Intermediate Similarity	NPD5494	Approved
0.7727	Intermediate Similarity	NPD2800	Approved
0.7727	Intermediate Similarity	NPD1243	Approved
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD4308	Phase 3
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7697	Intermediate Similarity	NPD2799	Discontinued
0.7671	Intermediate Similarity	NPD1470	Approved
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1512	Approved
0.7651	Intermediate Similarity	NPD7229	Phase 3
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD3764	Approved
0.7651	Intermediate Similarity	NPD3268	Approved
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7639	Intermediate Similarity	NPD1201	Approved
0.7635	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD2798	Approved
0.761	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4380	Phase 2
0.7574	Intermediate Similarity	NPD3818	Discontinued
0.756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6166	Phase 2
0.7548	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6273	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7533	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5408	Approved
0.7532	Intermediate Similarity	NPD5404	Approved
0.7532	Intermediate Similarity	NPD5405	Approved
0.7532	Intermediate Similarity	NPD5406	Approved
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5402	Approved
0.7485	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD1471	Phase 3
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1608	Approved
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4965	Approved
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5760	Phase 2
0.7439	Intermediate Similarity	NPD5761	Phase 2
0.7434	Intermediate Similarity	NPD4307	Phase 2
0.7432	Intermediate Similarity	NPD1203	Approved
0.741	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7394	Intermediate Similarity	NPD2296	Approved
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD7177	Discontinued
0.7365	Intermediate Similarity	NPD1283	Approved
0.7342	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7312	Intermediate Similarity	NPD6799	Approved
0.731	Intermediate Similarity	NPD1651	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4287	Approved
0.7299	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3817	Phase 2
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD919	Approved
0.726	Intermediate Similarity	NPD17	Approved
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8032	Phase 2
0.7248	Intermediate Similarity	NPD6696	Suspended
0.7248	Intermediate Similarity	NPD1876	Approved
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.723	Intermediate Similarity	NPD9717	Approved
0.723	Intermediate Similarity	NPD3972	Approved
0.7219	Intermediate Similarity	NPD6746	Phase 2
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD943	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4288	Approved
0.7184	Intermediate Similarity	NPD7074	Phase 3
0.7171	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7168	Intermediate Similarity	NPD7228	Approved
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7162	Intermediate Similarity	NPD1281	Approved
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5401	Approved
0.7151	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3019	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7054	Approved
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6971	Discontinued
0.7099	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2979	Phase 3
0.7092	Intermediate Similarity	NPD4750	Phase 3
0.7086	Intermediate Similarity	NPD7472	Approved
0.7073	Intermediate Similarity	NPD3869	Phase 3
0.7073	Intermediate Similarity	NPD3873	Phase 3
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6280	Approved
0.7066	Intermediate Similarity	NPD6279	Approved
0.7047	Intermediate Similarity	NPD1611	Approved
0.7045	Intermediate Similarity	NPD6797	Phase 2
0.7045	Intermediate Similarity	NPD5953	Discontinued
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6671	Approved
0.7029	Intermediate Similarity	NPD7286	Phase 2
0.7027	Intermediate Similarity	NPD2932	Approved
0.7027	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD3446	Phase 1
0.7006	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.6987	Remote Similarity	NPD4060	Phase 1
0.6987	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1613	Approved
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8127	Discontinued
0.6968	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6844	Discontinued

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