NPASS Compound

Structure

NPC149085 OpenBabel07101719252D 27 31 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0468 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0468 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -0.0000 3.0000 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 4.3776 0.4067 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 -0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0468 -0.3364 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 -0.0000 2.0000 0.0000 C 0 0 1 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 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 0.5000 0.0000 C 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 3.5686 -0.9945 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 24 1 0 0 0 0 3 24 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 15 2 0 0 0 0 7 20 2 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 10 14 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 21 2 0 0 0 0 13 16 1 0 0 0 0 13 22 2 0 0 0 0 14 1 1 6 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 9 1 1 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.19
Volume:	388.793
LogP:	7.472
LogD:	4.842
LogS:	-2.947
# Rotatable Bonds:	1
TPSA:	42.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	3.549
Fsp3:	0.417
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:	-4.865
MDCK Permeability:	1.5804786016815342e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.817
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	99.83999633789062%
Volume Distribution (VD):	2.68
Pgp-substrate:	1.7814804315567017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.716
CYP1A2-substrate:	0.717
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.179
CYP2C9-inhibitor:	0.638
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.474

ADMET: Excretion

Clearance (CL):	5.638
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.345
Human Hepatotoxicity (H-HT):	0.776
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.846
Carcinogencity:	0.568
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC149085

Natural Product ID:	NPC149085
*Common Name:**	Machaeriol B
IUPAC Name:	(6aS,9S,10aS)-3-(1-benzofuran-2-yl)-6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
Synonyms:	Machaeriol B
Standard InCHIKey:	HCVQRSCZRRQWTK-WBAXXEDZSA-N
Standard InCHI:	InChI=1S/C24H26O3/c1-14-8-9-18-17(10-14)23-19(25)11-16(13-22(23)27-24(18,2)3)21-12-15-6-4-5-7-20(15)26-21/h4-7,11-14,17-18,25H,8-10H2,1-3H3/t14-,17-,18-/m0/s1
SMILES:	C[C@H]1CC[C@H]2[C@H](C1)c1c(cc(cc1OC2(C)C)c1cc2ccccc2o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494038
PubChem CID:	10384052
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	5
Others	4

Activity Type	# Activity
Individual Protein	2
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	-3.0	%	PMID[505504]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	3.0	%	PMID[505504]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.72	ug.mL-1	PMID[505504]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.12	ug.mL-1	PMID[505504]
NPT2	Others	Unspecified		Ratio IC50	>	6.6	n.a.	PMID[505504]
NPT2	Others	Unspecified		Ratio IC50	>	40.0	n.a.	PMID[505504]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	5.0	ug.mL-1	PMID[505504]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4.5	ug.mL-1	PMID[505504]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.12	ug.mL-1	PMID[505505]

☑ 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 NPC149085 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	414
0.1-0.2	1562
0.2-0.3	3104
0.3-0.4	8530
0.4-0.5	10543
0.5-0.6	3822
0.6-0.7	6186
0.7-0.8	7427
0.8-0.85	1032
0.85-0.9	72
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC150215
0.96	High Similarity	NPC226287
0.9262	High Similarity	NPC13282
0.9226	High Similarity	NPC159508
0.9167	High Similarity	NPC112757
0.8961	High Similarity	NPC137100
0.8954	High Similarity	NPC72370
0.8924	High Similarity	NPC169471
0.8903	High Similarity	NPC246647
0.8903	High Similarity	NPC212967
0.8903	High Similarity	NPC96342
0.8903	High Similarity	NPC164110
0.8903	High Similarity	NPC268360
0.8896	High Similarity	NPC99199
0.8882	High Similarity	NPC167576
0.8839	High Similarity	NPC180924
0.8831	High Similarity	NPC472462
0.8831	High Similarity	NPC235333
0.8824	High Similarity	NPC23668
0.8824	High Similarity	NPC193976
0.8812	High Similarity	NPC253730
0.8812	High Similarity	NPC286230
0.8782	High Similarity	NPC158542
0.8782	High Similarity	NPC65504
0.8774	High Similarity	NPC148938
0.8774	High Similarity	NPC213936
0.8774	High Similarity	NPC297531
0.8766	High Similarity	NPC142308
0.8766	High Similarity	NPC207624
0.8758	High Similarity	NPC78335
0.8758	High Similarity	NPC230713
0.8712	High Similarity	NPC24748
0.8712	High Similarity	NPC59491
0.871	High Similarity	NPC213608
0.871	High Similarity	NPC1477
0.8701	High Similarity	NPC106372
0.8701	High Similarity	NPC58668
0.8701	High Similarity	NPC170169
0.8701	High Similarity	NPC115324
0.8693	High Similarity	NPC178202
0.8684	High Similarity	NPC77903
0.8684	High Similarity	NPC17101
0.8675	High Similarity	NPC98926
0.8645	High Similarity	NPC5871
0.8627	High Similarity	NPC272194
0.8614	High Similarity	NPC121888
0.8608	High Similarity	NPC40583
0.8608	High Similarity	NPC4950
0.8608	High Similarity	NPC472877
0.8608	High Similarity	NPC239118
0.8606	High Similarity	NPC101991
0.859	High Similarity	NPC329844
0.8581	High Similarity	NPC305965
0.8571	High Similarity	NPC474591
0.8571	High Similarity	NPC226644
0.8571	High Similarity	NPC221868
0.8571	High Similarity	NPC37208
0.8571	High Similarity	NPC70764
0.8571	High Similarity	NPC37226
0.8562	High Similarity	NPC3448
0.8562	High Similarity	NPC477239
0.8562	High Similarity	NPC17816
0.8562	High Similarity	NPC71055
0.8553	High Similarity	NPC155144
0.8543	High Similarity	NPC1534
0.8535	High Similarity	NPC198490
0.8509	High Similarity	NPC155640
0.8506	High Similarity	NPC135325
0.85	High Similarity	NPC74854
0.85	High Similarity	NPC30655
0.85	High Similarity	NPC137232
0.85	High Similarity	NPC45124
0.85	High Similarity	NPC18380
0.8497	Intermediate Similarity	NPC51641
0.8497	Intermediate Similarity	NPC210826
0.8497	Intermediate Similarity	NPC300267
0.8497	Intermediate Similarity	NPC469758
0.8497	Intermediate Similarity	NPC196114
0.8491	Intermediate Similarity	NPC244750
0.8491	Intermediate Similarity	NPC186113
0.8487	Intermediate Similarity	NPC225884
0.8472	Intermediate Similarity	NPC222108
0.8472	Intermediate Similarity	NPC96719
0.8471	Intermediate Similarity	NPC178964
0.8471	Intermediate Similarity	NPC135522
0.8471	Intermediate Similarity	NPC183874
0.8471	Intermediate Similarity	NPC280530
0.8471	Intermediate Similarity	NPC95842
0.8462	Intermediate Similarity	NPC258249
0.8462	Intermediate Similarity	NPC474417
0.8462	Intermediate Similarity	NPC39819
0.8462	Intermediate Similarity	NPC149526
0.8457	Intermediate Similarity	NPC136641
0.8456	Intermediate Similarity	NPC62735
0.8452	Intermediate Similarity	NPC65775
0.8452	Intermediate Similarity	NPC329933
0.8452	Intermediate Similarity	NPC10027
0.8447	Intermediate Similarity	NPC477528
0.8447	Intermediate Similarity	NPC473961
0.8442	Intermediate Similarity	NPC130581
0.8442	Intermediate Similarity	NPC12148
0.8438	Intermediate Similarity	NPC470810
0.8438	Intermediate Similarity	NPC184326
0.8438	Intermediate Similarity	NPC115432
0.8438	Intermediate Similarity	NPC260296
0.8438	Intermediate Similarity	NPC292863
0.8434	Intermediate Similarity	NPC300657
0.8431	Intermediate Similarity	NPC230943
0.8431	Intermediate Similarity	NPC469764
0.8428	Intermediate Similarity	NPC296957
0.8428	Intermediate Similarity	NPC260902
0.8421	Intermediate Similarity	NPC3732
0.8418	Intermediate Similarity	NPC226656
0.8418	Intermediate Similarity	NPC66508
0.8411	Intermediate Similarity	NPC145673
0.8408	Intermediate Similarity	NPC217447
0.8408	Intermediate Similarity	NPC40356
0.8408	Intermediate Similarity	NPC87708
0.8408	Intermediate Similarity	NPC142527
0.8408	Intermediate Similarity	NPC154683
0.8405	Intermediate Similarity	NPC277480
0.8405	Intermediate Similarity	NPC53640
0.84	Intermediate Similarity	NPC18457
0.8397	Intermediate Similarity	NPC471115
0.8397	Intermediate Similarity	NPC120105
0.8397	Intermediate Similarity	NPC29777
0.8397	Intermediate Similarity	NPC227122
0.8397	Intermediate Similarity	NPC101957
0.8395	Intermediate Similarity	NPC38591
0.8395	Intermediate Similarity	NPC473009
0.8387	Intermediate Similarity	NPC37135
0.8387	Intermediate Similarity	NPC35150
0.8387	Intermediate Similarity	NPC39195
0.8387	Intermediate Similarity	NPC472841
0.8387	Intermediate Similarity	NPC106328
0.8387	Intermediate Similarity	NPC186397
0.8385	Intermediate Similarity	NPC476929
0.8385	Intermediate Similarity	NPC301256
0.8385	Intermediate Similarity	NPC312273
0.8377	Intermediate Similarity	NPC473135
0.8377	Intermediate Similarity	NPC477955
0.8377	Intermediate Similarity	NPC299011
0.8377	Intermediate Similarity	NPC470676
0.8377	Intermediate Similarity	NPC473132
0.8375	Intermediate Similarity	NPC218818
0.8375	Intermediate Similarity	NPC474373
0.8375	Intermediate Similarity	NPC195167
0.8375	Intermediate Similarity	NPC324736
0.8375	Intermediate Similarity	NPC177650
0.8373	Intermediate Similarity	NPC65885
0.8373	Intermediate Similarity	NPC310794
0.8366	Intermediate Similarity	NPC302181
0.8365	Intermediate Similarity	NPC247677
0.8365	Intermediate Similarity	NPC160015
0.8364	Intermediate Similarity	NPC476641
0.8364	Intermediate Similarity	NPC131866
0.8354	Intermediate Similarity	NPC214632
0.8354	Intermediate Similarity	NPC122365
0.8354	Intermediate Similarity	NPC476459
0.8354	Intermediate Similarity	NPC42458
0.8354	Intermediate Similarity	NPC210942
0.8354	Intermediate Similarity	NPC169990
0.8354	Intermediate Similarity	NPC50394
0.8354	Intermediate Similarity	NPC158261
0.8344	Intermediate Similarity	NPC37183
0.8344	Intermediate Similarity	NPC72958
0.8344	Intermediate Similarity	NPC46564
0.8344	Intermediate Similarity	NPC207346
0.8344	Intermediate Similarity	NPC473499
0.8344	Intermediate Similarity	NPC232645
0.8344	Intermediate Similarity	NPC473010
0.8344	Intermediate Similarity	NPC478148
0.8333	Intermediate Similarity	NPC158338
0.8333	Intermediate Similarity	NPC15374
0.8333	Intermediate Similarity	NPC97028
0.8333	Intermediate Similarity	NPC223988
0.8333	Intermediate Similarity	NPC97029
0.8333	Intermediate Similarity	NPC474052
0.8333	Intermediate Similarity	NPC39929
0.8333	Intermediate Similarity	NPC100985
0.8333	Intermediate Similarity	NPC65589
0.8333	Intermediate Similarity	NPC288036
0.8333	Intermediate Similarity	NPC266499
0.8333	Intermediate Similarity	NPC296030
0.8333	Intermediate Similarity	NPC473012
0.8333	Intermediate Similarity	NPC475106
0.8323	Intermediate Similarity	NPC34802
0.8323	Intermediate Similarity	NPC186325
0.8323	Intermediate Similarity	NPC308200
0.8323	Intermediate Similarity	NPC220582
0.8323	Intermediate Similarity	NPC312993
0.8323	Intermediate Similarity	NPC304839
0.8323	Intermediate Similarity	NPC227906
0.8322	Intermediate Similarity	NPC163029
0.8313	Intermediate Similarity	NPC272196
0.8313	Intermediate Similarity	NPC196448
0.8313	Intermediate Similarity	NPC44199
0.8313	Intermediate Similarity	NPC201127
0.8312	Intermediate Similarity	NPC303185
0.8312	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 NPC149085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	917
0.2-0.3	1310
0.3-0.4	2524
0.4-0.5	2214
0.5-0.6	1185
0.6-0.7	454
0.7-0.8	165
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
0.8544	High Similarity	NPD3749	Approved
0.8389	Intermediate Similarity	NPD6099	Approved
0.8389	Intermediate Similarity	NPD6100	Approved
0.8289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6959	Discontinued
0.8219	Intermediate Similarity	NPD4625	Phase 3
0.8194	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD3750	Approved
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3226	Approved
0.7974	Intermediate Similarity	NPD2346	Discontinued
0.7974	Intermediate Similarity	NPD2344	Approved
0.7974	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7473	Discontinued
0.7962	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4749	Approved
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7819	Suspended
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7888	Intermediate Similarity	NPD7411	Suspended
0.7879	Intermediate Similarity	NPD5494	Approved
0.7843	Intermediate Similarity	NPD3748	Approved
0.7829	Intermediate Similarity	NPD1607	Approved
0.7806	Intermediate Similarity	NPD1549	Phase 2
0.78	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD2309	Approved
0.7742	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD1934	Approved
0.7716	Intermediate Similarity	NPD4380	Phase 2
0.7707	Intermediate Similarity	NPD7003	Approved
0.7697	Intermediate Similarity	NPD1240	Approved
0.7697	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7683	Intermediate Similarity	NPD2801	Approved
0.7682	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7677	Intermediate Similarity	NPD2796	Approved
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7673	Intermediate Similarity	NPD1511	Approved
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.7643	Intermediate Similarity	NPD2800	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4308	Phase 3
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1510	Phase 2
0.7584	Intermediate Similarity	NPD2797	Approved
0.7578	Intermediate Similarity	NPD1512	Approved
0.7574	Intermediate Similarity	NPD7229	Phase 3
0.7545	Intermediate Similarity	NPD7075	Discontinued
0.7545	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD920	Approved
0.753	Intermediate Similarity	NPD5402	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7528	Intermediate Similarity	NPD4287	Approved
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5761	Phase 2
0.747	Intermediate Similarity	NPD5760	Phase 2
0.7469	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1470	Approved
0.7452	Intermediate Similarity	NPD5408	Approved
0.7452	Intermediate Similarity	NPD5406	Approved
0.7452	Intermediate Similarity	NPD5404	Approved
0.7452	Intermediate Similarity	NPD2935	Discontinued
0.7452	Intermediate Similarity	NPD5405	Approved
0.7451	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7432	Intermediate Similarity	NPD1201	Approved
0.7417	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7399	Intermediate Similarity	NPD7177	Discontinued
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1608	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4307	Phase 2
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5403	Approved
0.7314	Intermediate Similarity	NPD7074	Phase 3
0.731	Intermediate Similarity	NPD1247	Approved
0.7299	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7296	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7257	Intermediate Similarity	NPD7054	Approved
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7239	Intermediate Similarity	NPD6799	Approved
0.7237	Intermediate Similarity	NPD1203	Approved
0.7232	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4288	Approved
0.7219	Intermediate Similarity	NPD2296	Approved
0.7219	Intermediate Similarity	NPD3817	Phase 2
0.7216	Intermediate Similarity	NPD7472	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6801	Discontinued
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5401	Approved
0.7193	Intermediate Similarity	NPD919	Approved
0.7191	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD17	Approved
0.7175	Intermediate Similarity	NPD6797	Phase 2
0.7171	Intermediate Similarity	NPD1283	Approved
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7151	Intermediate Similarity	NPD6746	Phase 2
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3266	Approved
0.7124	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD411	Approved
0.7114	Intermediate Similarity	NPD1651	Approved
0.7095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7808	Phase 3
0.7091	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD447	Suspended
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7075	Intermediate Similarity	NPD6671	Approved
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.707	Intermediate Similarity	NPD8032	Phase 2
0.7059	Intermediate Similarity	NPD3225	Approved
0.7059	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD1548	Phase 1
0.7045	Intermediate Similarity	NPD3446	Phase 1
0.7039	Intermediate Similarity	NPD3972	Approved
0.7039	Intermediate Similarity	NPD9717	Approved
0.7035	Intermediate Similarity	NPD6971	Discontinued
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD943	Approved
0.7025	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1613	Approved
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD7577	Discontinued
0.7	Intermediate Similarity	NPD6823	Phase 2
0.6989	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6832	Phase 2
0.6983	Remote Similarity	NPD5953	Discontinued
0.6981	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1281	Approved
0.6966	Remote Similarity	NPD7286	Phase 2
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	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