NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	368.16
Volume:	386.258
LogP:	5.807
LogD:	4.248
LogS:	-3.763
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	3.417
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	1.863543366198428e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	90.16124725341797%
Volume Distribution (VD):	0.613
Pgp-substrate:	9.969942092895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.503
CYP2C9-substrate:	0.316
CYP2D6-inhibitor:	0.797
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	5.567
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.385
Carcinogencity:	0.765
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.832

Download Data

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

Natural Product: NPC477691

Natural Product ID:	NPC477691
*Common Name:**	Busseihydroquinone C
IUPAC Name:	7-hydroxy-10-methoxy-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-8-carboxylic acid
Synonyms:	Busseihydroquinone C
Standard InCHIKey:	MPFRBGNULMTVEA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O5/c1-13(2)6-5-10-22(3)11-9-14-17(27-22)8-7-15-19(14)18(26-4)12-16(20(15)23)21(24)25/h6-9,11-12,23H,5,10H2,1-4H3,(H,24,25)
SMILES:	COc1cc(C(=O)O)c(c2c1c1C=CC(Oc1cc2)(C)CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071295
PubChem CID:	60201022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33631	Pentas bussei	Species	Rubiaceae	Eukaryota	Roots	Mombasa, coastal region of Kenya	2010-JUL	PMID[22709138]
NPO6195	Rhodopentas bussei	Species	Rubiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[27518587]
NPO41025	Pentas parvifolia	Species	Rubiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[27518587]
NPO6195	Rhodopentas bussei	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	2
LD50	2
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	LD50	>	271.62	uM	PMID[534203]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	32650.0	nM	PMID[534203]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	60080.0	nM	PMID[534203]
NPT2	Others	Unspecified		Selectivity Index	>	8.32	n.a.	PMID[534203]
NPT2	Others	Unspecified		Selectivity Index	>	4.52	n.a.	PMID[534203]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LD50	=	48.4	uM	PMID[534204]

☑ 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 NPC477691 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	364
0.1-0.2	1591
0.2-0.3	3527
0.3-0.4	8325
0.4-0.5	10068
0.5-0.6	3515
0.6-0.7	5809
0.7-0.8	6991
0.8-0.85	2220
0.85-0.9	273
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC477690
0.9603	High Similarity	NPC477692
0.9521	High Similarity	NPC60389
0.9481	High Similarity	NPC477689
0.9388	High Similarity	NPC211565
0.9272	High Similarity	NPC175978
0.9156	High Similarity	NPC44199
0.9145	High Similarity	NPC217447
0.9085	High Similarity	NPC135522
0.9057	High Similarity	NPC76647
0.9007	High Similarity	NPC37139
0.8968	High Similarity	NPC146211
0.8961	High Similarity	NPC280530
0.8961	High Similarity	NPC169990
0.8961	High Similarity	NPC95842
0.8961	High Similarity	NPC210942
0.8961	High Similarity	NPC178964
0.8961	High Similarity	NPC329844
0.8947	High Similarity	NPC97028
0.8947	High Similarity	NPC233267
0.8947	High Similarity	NPC288036
0.8947	High Similarity	NPC65589
0.8947	High Similarity	NPC97029
0.8947	High Similarity	NPC10027
0.8947	High Similarity	NPC158338
0.8947	High Similarity	NPC65775
0.8947	High Similarity	NPC100985
0.8947	High Similarity	NPC70764
0.8947	High Similarity	NPC291049
0.8917	High Similarity	NPC143050
0.891	High Similarity	NPC263483
0.8896	High Similarity	NPC281272
0.8896	High Similarity	NPC273483
0.8896	High Similarity	NPC271681
0.8889	High Similarity	NPC295036
0.8889	High Similarity	NPC158866
0.8889	High Similarity	NPC227122
0.8882	High Similarity	NPC27221
0.8882	High Similarity	NPC256672
0.8882	High Similarity	NPC105415
0.8882	High Similarity	NPC7025
0.8875	High Similarity	NPC30027
0.8874	High Similarity	NPC163846
0.8874	High Similarity	NPC225173
0.8861	High Similarity	NPC66288
0.8854	High Similarity	NPC186113
0.8854	High Similarity	NPC474373
0.8831	High Similarity	NPC258249
0.8831	High Similarity	NPC39819
0.8831	High Similarity	NPC474417
0.8831	High Similarity	NPC133856
0.8831	High Similarity	NPC149526
0.8827	High Similarity	NPC109827
0.8827	High Similarity	NPC124470
0.8824	High Similarity	NPC266499
0.882	High Similarity	NPC234331
0.8816	High Similarity	NPC125801
0.8816	High Similarity	NPC22005
0.8816	High Similarity	NPC7943
0.8816	High Similarity	NPC123202
0.8805	High Similarity	NPC473961
0.8797	High Similarity	NPC47623
0.8792	High Similarity	NPC124365
0.879	High Similarity	NPC164110
0.879	High Similarity	NPC212967
0.879	High Similarity	NPC246647
0.879	High Similarity	NPC268360
0.879	High Similarity	NPC96342
0.8782	High Similarity	NPC166054
0.8782	High Similarity	NPC66029
0.8782	High Similarity	NPC55662
0.8774	High Similarity	NPC40356
0.8774	High Similarity	NPC154683
0.8766	High Similarity	NPC294646
0.8766	High Similarity	NPC120105
0.8766	High Similarity	NPC150928
0.8766	High Similarity	NPC101957
0.8766	High Similarity	NPC470107
0.8766	High Similarity	NPC119929
0.8765	High Similarity	NPC99613
0.8765	High Similarity	NPC49487
0.8758	High Similarity	NPC37135
0.8758	High Similarity	NPC186397
0.8758	High Similarity	NPC172329
0.8758	High Similarity	NPC29160
0.8758	High Similarity	NPC5537
0.8758	High Similarity	NPC2569
0.875	High Similarity	NPC207690
0.875	High Similarity	NPC300540
0.875	High Similarity	NPC270837
0.8742	High Similarity	NPC274085
0.8742	High Similarity	NPC89664
0.8742	High Similarity	NPC24761
0.8726	High Similarity	NPC180924
0.8726	High Similarity	NPC474360
0.8725	High Similarity	NPC168471
0.8718	High Similarity	NPC472799
0.8712	High Similarity	NPC313304
0.8712	High Similarity	NPC241874
0.871	High Similarity	NPC478148
0.871	High Similarity	NPC72958
0.871	High Similarity	NPC232645
0.8701	High Similarity	NPC329933
0.8701	High Similarity	NPC223988
0.8693	High Similarity	NPC71055
0.8693	High Similarity	NPC34802
0.8688	High Similarity	NPC144843
0.8688	High Similarity	NPC294965
0.8688	High Similarity	NPC329760
0.8688	High Similarity	NPC229632
0.8684	High Similarity	NPC134621
0.8684	High Similarity	NPC469953
0.8684	High Similarity	NPC311741
0.8684	High Similarity	NPC234629
0.8675	High Similarity	NPC476473
0.8671	High Similarity	NPC67197
0.8671	High Similarity	NPC476981
0.8667	High Similarity	NPC470454
0.8667	High Similarity	NPC199533
0.8662	High Similarity	NPC148938
0.8662	High Similarity	NPC149618
0.8662	High Similarity	NPC99199
0.8662	High Similarity	NPC89625
0.8659	High Similarity	NPC158226
0.8658	High Similarity	NPC1268
0.8654	High Similarity	NPC87708
0.8654	High Similarity	NPC474843
0.865	High Similarity	NPC165979
0.865	High Similarity	NPC163130
0.8645	High Similarity	NPC325983
0.8645	High Similarity	NPC37348
0.8645	High Similarity	NPC202595
0.8645	High Similarity	NPC13282
0.8645	High Similarity	NPC474660
0.8645	High Similarity	NPC205766
0.8642	High Similarity	NPC37870
0.8634	High Similarity	NPC474350
0.8634	High Similarity	NPC156082
0.8634	High Similarity	NPC197168
0.8627	High Similarity	NPC469758
0.8627	High Similarity	NPC267509
0.8627	High Similarity	NPC237208
0.8627	High Similarity	NPC196114
0.8627	High Similarity	NPC473927
0.8618	High Similarity	NPC95123
0.8618	High Similarity	NPC189650
0.8618	High Similarity	NPC66404
0.8618	High Similarity	NPC260152
0.8618	High Similarity	NPC295696
0.8618	High Similarity	NPC71739
0.8618	High Similarity	NPC471305
0.8616	High Similarity	NPC45846
0.8609	High Similarity	NPC250755
0.8609	High Similarity	NPC474300
0.8608	High Similarity	NPC4547
0.8606	High Similarity	NPC181523
0.86	High Similarity	NPC183642
0.86	High Similarity	NPC310370
0.8599	High Similarity	NPC472462
0.8599	High Similarity	NPC235333
0.8599	High Similarity	NPC214632
0.8599	High Similarity	NPC72370
0.8589	High Similarity	NPC473094
0.8589	High Similarity	NPC225419
0.8581	High Similarity	NPC269420
0.8581	High Similarity	NPC474052
0.8581	High Similarity	NPC115861
0.858	High Similarity	NPC239752
0.858	High Similarity	NPC472450
0.858	High Similarity	NPC112981
0.858	High Similarity	NPC275780
0.858	High Similarity	NPC25361
0.8571	High Similarity	NPC137296
0.8571	High Similarity	NPC472402
0.8571	High Similarity	NPC118027
0.8571	High Similarity	NPC56433
0.8571	High Similarity	NPC312929
0.8571	High Similarity	NPC190648
0.8571	High Similarity	NPC245584
0.8571	High Similarity	NPC126767
0.8571	High Similarity	NPC470694
0.8571	High Similarity	NPC289042
0.8562	High Similarity	NPC469764
0.8562	High Similarity	NPC29577
0.8562	High Similarity	NPC476980
0.8562	High Similarity	NPC470810
0.8562	High Similarity	NPC284495
0.8562	High Similarity	NPC32470
0.8562	High Similarity	NPC119224
0.8562	High Similarity	NPC478019
0.8562	High Similarity	NPC186325
0.8562	High Similarity	NPC131766
0.8554	High Similarity	NPC289147
0.8553	High Similarity	NPC158542
0.8553	High Similarity	NPC226636
0.8553	High Similarity	NPC84266
0.8553	High Similarity	NPC165977
0.8553	High Similarity	NPC196448
0.8553	High Similarity	NPC11561
0.8553	High Similarity	NPC217677

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 NPC477691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	982
0.2-0.3	1513
0.3-0.4	2457
0.4-0.5	1961
0.5-0.6	1172
0.6-0.7	486
0.7-0.8	214
0.8-0.85	28
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD2935	Discontinued
0.8716	High Similarity	NPD2346	Discontinued
0.8701	High Similarity	NPD3226	Approved
0.8599	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD6232	Discontinued
0.8442	Intermediate Similarity	NPD2532	Approved
0.8442	Intermediate Similarity	NPD2533	Approved
0.8442	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2534	Approved
0.8424	Intermediate Similarity	NPD5844	Phase 1
0.8421	Intermediate Similarity	NPD3750	Approved
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8375	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD2799	Discontinued
0.8299	Intermediate Similarity	NPD2313	Discontinued
0.8289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6959	Discontinued
0.8278	Intermediate Similarity	NPD5406	Approved
0.8278	Intermediate Similarity	NPD5408	Approved
0.8278	Intermediate Similarity	NPD5405	Approved
0.8278	Intermediate Similarity	NPD5404	Approved
0.825	Intermediate Similarity	NPD2801	Approved
0.8228	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3749	Approved
0.8205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8137	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8092	Intermediate Similarity	NPD3748	Approved
0.8092	Intermediate Similarity	NPD4308	Phase 3
0.8086	Intermediate Similarity	NPD5402	Approved
0.8065	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7003	Approved
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8057	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1510	Phase 2
0.7965	Intermediate Similarity	NPD8313	Approved
0.7965	Intermediate Similarity	NPD8312	Approved
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.7961	Intermediate Similarity	NPD1607	Approved
0.7959	Intermediate Similarity	NPD1203	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7935	Intermediate Similarity	NPD1549	Phase 2
0.7933	Intermediate Similarity	NPD3764	Approved
0.7922	Intermediate Similarity	NPD2796	Approved
0.7911	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD5494	Approved
0.7891	Intermediate Similarity	NPD1283	Approved
0.7875	Intermediate Similarity	NPD920	Approved
0.7871	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4625	Phase 3
0.7866	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1934	Approved
0.7838	Intermediate Similarity	NPD2797	Approved
0.7829	Intermediate Similarity	NPD1240	Approved
0.7829	Intermediate Similarity	NPD4307	Phase 2
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD411	Approved
0.7812	Intermediate Similarity	NPD1512	Approved
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.78	Intermediate Similarity	NPD6832	Phase 2
0.7799	Intermediate Similarity	NPD6799	Approved
0.7798	Intermediate Similarity	NPD5710	Approved
0.7798	Intermediate Similarity	NPD5711	Approved
0.7778	Intermediate Similarity	NPD447	Suspended
0.7778	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1243	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2344	Approved
0.7755	Intermediate Similarity	NPD9717	Approved
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7177	Discontinued
0.7719	Intermediate Similarity	NPD3818	Discontinued
0.7718	Intermediate Similarity	NPD1470	Approved
0.7712	Intermediate Similarity	NPD2979	Phase 3
0.7711	Intermediate Similarity	NPD3882	Suspended
0.7702	Intermediate Similarity	NPD6273	Approved
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3268	Approved
0.7688	Intermediate Similarity	NPD7390	Discontinued
0.7687	Intermediate Similarity	NPD1281	Approved
0.7687	Intermediate Similarity	NPD1611	Approved
0.7671	Intermediate Similarity	NPD4626	Approved
0.7667	Intermediate Similarity	NPD2798	Approved
0.7658	Intermediate Similarity	NPD2800	Approved
0.7654	Intermediate Similarity	NPD5403	Approved
0.7643	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7033	Discontinued
0.7627	Intermediate Similarity	NPD8150	Discontinued
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7435	Discontinued
0.7619	Intermediate Similarity	NPD7783	Phase 2
0.7619	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1164	Approved
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.7588	Intermediate Similarity	NPD7229	Phase 3
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.7582	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7572	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD1201	Approved
0.7562	Intermediate Similarity	NPD2309	Approved
0.7554	Intermediate Similarity	NPD6777	Approved
0.7554	Intermediate Similarity	NPD6776	Approved
0.7554	Intermediate Similarity	NPD6780	Approved
0.7554	Intermediate Similarity	NPD6778	Approved
0.7554	Intermediate Similarity	NPD6782	Approved
0.7554	Intermediate Similarity	NPD6779	Approved
0.7554	Intermediate Similarity	NPD6781	Approved
0.7545	Intermediate Similarity	NPD4288	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7531	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1247	Approved
0.7517	Intermediate Similarity	NPD1608	Approved
0.7515	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD5691	Approved
0.7483	Intermediate Similarity	NPD1651	Approved
0.7473	Intermediate Similarity	NPD6823	Phase 2
0.7471	Intermediate Similarity	NPD7054	Approved
0.7468	Intermediate Similarity	NPD2438	Suspended
0.7468	Intermediate Similarity	NPD4476	Approved
0.7468	Intermediate Similarity	NPD4477	Approved
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7436	Intermediate Similarity	NPD1933	Approved
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7433	Intermediate Similarity	NPD7697	Approved
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD7074	Phase 3
0.7429	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7417	Intermediate Similarity	NPD3225	Approved
0.7417	Intermediate Similarity	NPD6696	Suspended
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD1481	Phase 2
0.7397	Intermediate Similarity	NPD9493	Approved
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7396	Intermediate Similarity	NPD4965	Approved
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.7382	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7874	Approved
0.7368	Intermediate Similarity	NPD3267	Approved
0.7368	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2531	Phase 2
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD1535	Discovery
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1019	Discontinued
0.7315	Intermediate Similarity	NPD17	Approved
0.7312	Intermediate Similarity	NPD1471	Phase 3
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7289	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7283	Intermediate Similarity	NPD6534	Approved
0.7283	Intermediate Similarity	NPD6535	Approved
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7277	Intermediate Similarity	NPD7701	Phase 2
0.7267	Intermediate Similarity	NPD3496	Discontinued
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4287	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7241	Intermediate Similarity	NPD3926	Phase 2
0.724	Intermediate Similarity	NPD8151	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