NPASS Compound

Structure

NPC469642 OpenBabel07101718312D 27 29 0 0 1 0 0 0 0 0999 V2000 1.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8785 -3.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6285 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3605 -0.5294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4945 -0.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6581 -3.2102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7921 -2.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 -1.6275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3605 0.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4013 -2.5411 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 23 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 19 2 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 6 0 0 0 22 27 1 0 0 0 0 23 4 1 6 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	400.037
LogP:	5.558
LogD:	4.268
LogS:	-5.755
# Rotatable Bonds:	7
TPSA:	51.83
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	4.189
Fsp3:	0.478
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:	-4.763
MDCK Permeability:	2.4084714823402464e-05
Pgp-inhibitor:	0.615
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.737

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	98.18949127197266%
Volume Distribution (VD):	0.47
Pgp-substrate:	0.8094810843467712%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.533
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.964
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.843
CYP3A4-substrate:	0.533

ADMET: Excretion

Clearance (CL):	8.348
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.796
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.482
Carcinogencity:	0.063
Eye Corrosion:	0.012
Eye Irritation:	0.439
Respiratory Toxicity:	0.32

Download Data

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

Natural Product: NPC469642

Natural Product ID:	NPC469642
*Common Name:**	Capillobenzofuranol
IUPAC Name:	(2S)-2-[(E,2R)-2-methoxy-6-methyl-7-(4-methylfuran-2-yl)hept-5-en-2-yl]-6-methyl-2,3-dihydro-1-benzofuran-5-ol
Synonyms:	Capillobenzofuranol
Standard InCHIKey:	GSAYAGNITKAJHN-IBENBWMUSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-15(9-19-10-16(2)14-26-19)7-6-8-23(4,25-5)22-13-18-12-20(24)17(3)11-21(18)27-22/h7,10-12,14,22,24H,6,8-9,13H2,1-5H3/b15-7+/t22-,23+/m0/s1
SMILES:	CC1=CC2=C(CC(O2)C(C)(CCC=C(C)CC3=CC(=CO3)C)OC)C=C1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095582
PubChem CID:	46886866
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087604]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155971]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964704]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	13500.0	nM	PMID[536917]

☑ 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 NPC469642 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	338
0.1-0.2	1453
0.2-0.3	3792
0.3-0.4	10322
0.4-0.5	8668
0.5-0.6	3801
0.6-0.7	8682
0.7-0.8	5601
0.8-0.85	32
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.927	High Similarity	NPC265793
0.9071	High Similarity	NPC130976
0.9	High Similarity	NPC64157
0.9	High Similarity	NPC278832
0.8741	High Similarity	NPC98395
0.8618	High Similarity	NPC84721
0.8523	High Similarity	NPC308799
0.8497	Intermediate Similarity	NPC290927
0.8467	Intermediate Similarity	NPC113428
0.8467	Intermediate Similarity	NPC61284
0.8377	Intermediate Similarity	NPC470331
0.8344	Intermediate Similarity	NPC220582
0.8344	Intermediate Similarity	NPC304839
0.8291	Intermediate Similarity	NPC269117
0.8224	Intermediate Similarity	NPC14875
0.82	Intermediate Similarity	NPC158871
0.8194	Intermediate Similarity	NPC131121
0.8187	Intermediate Similarity	NPC308156
0.8176	Intermediate Similarity	NPC475045
0.8176	Intermediate Similarity	NPC112757
0.8165	Intermediate Similarity	NPC226287
0.8151	Intermediate Similarity	NPC204592
0.8133	Intermediate Similarity	NPC329493
0.8121	Intermediate Similarity	NPC475063
0.8121	Intermediate Similarity	NPC475044
0.8108	Intermediate Similarity	NPC475005
0.8108	Intermediate Similarity	NPC474943
0.8095	Intermediate Similarity	NPC473268
0.8089	Intermediate Similarity	NPC474542
0.8089	Intermediate Similarity	NPC300757
0.8089	Intermediate Similarity	NPC180901
0.8086	Intermediate Similarity	NPC53640
0.8086	Intermediate Similarity	NPC255787
0.8086	Intermediate Similarity	NPC291742
0.8082	Intermediate Similarity	NPC209858
0.8071	Intermediate Similarity	NPC118853
0.8069	Intermediate Similarity	NPC118253
0.8065	Intermediate Similarity	NPC13282
0.8065	Intermediate Similarity	NPC475890
0.8065	Intermediate Similarity	NPC167576
0.8065	Intermediate Similarity	NPC475717
0.8065	Intermediate Similarity	NPC472421
0.8063	Intermediate Similarity	NPC30655
0.8063	Intermediate Similarity	NPC74854
0.8063	Intermediate Similarity	NPC45124
0.8063	Intermediate Similarity	NPC24761
0.8054	Intermediate Similarity	NPC475012
0.8039	Intermediate Similarity	NPC469758
0.8038	Intermediate Similarity	NPC45131
0.8027	Intermediate Similarity	NPC475011
0.8027	Intermediate Similarity	NPC475029
0.8027	Intermediate Similarity	NPC476018
0.8026	Intermediate Similarity	NPC213900
0.8026	Intermediate Similarity	NPC89664
0.8026	Intermediate Similarity	NPC274085
0.8025	Intermediate Similarity	NPC72370
0.8025	Intermediate Similarity	NPC291110
0.8025	Intermediate Similarity	NPC301233
0.8025	Intermediate Similarity	NPC41689
0.8014	Intermediate Similarity	NPC106247
0.8014	Intermediate Similarity	NPC147896
0.8013	Intermediate Similarity	NPC149085
0.8013	Intermediate Similarity	NPC472423
0.8013	Intermediate Similarity	NPC171870
0.8013	Intermediate Similarity	NPC474744
0.8013	Intermediate Similarity	NPC474772
0.8	Intermediate Similarity	NPC470810
0.8	Intermediate Similarity	NPC247964
0.7987	Intermediate Similarity	NPC469425
0.7987	Intermediate Similarity	NPC196448
0.7987	Intermediate Similarity	NPC476025
0.7987	Intermediate Similarity	NPC150215
0.7987	Intermediate Similarity	NPC475028
0.7987	Intermediate Similarity	NPC17816
0.7987	Intermediate Similarity	NPC44199
0.7987	Intermediate Similarity	NPC123153
0.7987	Intermediate Similarity	NPC62735
0.7986	Intermediate Similarity	NPC475529
0.7975	Intermediate Similarity	NPC326910
0.7975	Intermediate Similarity	NPC268008
0.7974	Intermediate Similarity	NPC287495
0.7974	Intermediate Similarity	NPC9370
0.7974	Intermediate Similarity	NPC98926
0.7974	Intermediate Similarity	NPC469764
0.7973	Intermediate Similarity	NPC163029
0.7973	Intermediate Similarity	NPC215109
0.7973	Intermediate Similarity	NPC170604
0.7963	Intermediate Similarity	NPC472582
0.7962	Intermediate Similarity	NPC34965
0.7962	Intermediate Similarity	NPC253904
0.7962	Intermediate Similarity	NPC321363
0.7962	Intermediate Similarity	NPC473996
0.7962	Intermediate Similarity	NPC75069
0.7962	Intermediate Similarity	NPC183536
0.7962	Intermediate Similarity	NPC327269
0.7962	Intermediate Similarity	NPC476238
0.7962	Intermediate Similarity	NPC60211
0.7962	Intermediate Similarity	NPC31627
0.7961	Intermediate Similarity	NPC307346
0.7961	Intermediate Similarity	NPC267004
0.7961	Intermediate Similarity	NPC261733
0.7961	Intermediate Similarity	NPC218712
0.7961	Intermediate Similarity	NPC130206
0.7949	Intermediate Similarity	NPC213382
0.7949	Intermediate Similarity	NPC164527
0.7947	Intermediate Similarity	NPC145673
0.7947	Intermediate Similarity	NPC184053
0.7947	Intermediate Similarity	NPC263337
0.7937	Intermediate Similarity	NPC477692
0.7937	Intermediate Similarity	NPC472877
0.7937	Intermediate Similarity	NPC472299
0.7937	Intermediate Similarity	NPC196879
0.7935	Intermediate Similarity	NPC191634
0.7933	Intermediate Similarity	NPC268691
0.7929	Intermediate Similarity	NPC476165
0.7927	Intermediate Similarity	NPC472660
0.7925	Intermediate Similarity	NPC261090
0.7925	Intermediate Similarity	NPC195954
0.7925	Intermediate Similarity	NPC180924
0.7925	Intermediate Similarity	NPC7059
0.7922	Intermediate Similarity	NPC130176
0.7922	Intermediate Similarity	NPC196114
0.7922	Intermediate Similarity	NPC99454
0.7914	Intermediate Similarity	NPC300053
0.7911	Intermediate Similarity	NPC303950
0.7911	Intermediate Similarity	NPC183874
0.7911	Intermediate Similarity	NPC280937
0.7911	Intermediate Similarity	NPC122365
0.7908	Intermediate Similarity	NPC469385
0.7905	Intermediate Similarity	NPC303217
0.7904	Intermediate Similarity	NPC290304
0.7904	Intermediate Similarity	NPC236327
0.7901	Intermediate Similarity	NPC84515
0.7901	Intermediate Similarity	NPC312056
0.7901	Intermediate Similarity	NPC81679
0.7898	Intermediate Similarity	NPC58668
0.7898	Intermediate Similarity	NPC472580
0.7898	Intermediate Similarity	NPC106372
0.7898	Intermediate Similarity	NPC472636
0.7898	Intermediate Similarity	NPC471675
0.7898	Intermediate Similarity	NPC170169
0.7895	Intermediate Similarity	NPC27220
0.7895	Intermediate Similarity	NPC74397
0.7891	Intermediate Similarity	NPC470871
0.7888	Intermediate Similarity	NPC328102
0.7888	Intermediate Similarity	NPC471976
0.7887	Intermediate Similarity	NPC190086
0.7887	Intermediate Similarity	NPC4012
0.7887	Intermediate Similarity	NPC276962
0.7885	Intermediate Similarity	NPC285527
0.7885	Intermediate Similarity	NPC228842
0.7885	Intermediate Similarity	NPC178202
0.7885	Intermediate Similarity	NPC106334
0.7885	Intermediate Similarity	NPC474052
0.7881	Intermediate Similarity	NPC477537
0.7879	Intermediate Similarity	NPC211309
0.7877	Intermediate Similarity	NPC473982
0.7877	Intermediate Similarity	NPC471544
0.7877	Intermediate Similarity	NPC141549
0.7877	Intermediate Similarity	NPC45358
0.7877	Intermediate Similarity	NPC473344
0.7877	Intermediate Similarity	NPC474143
0.7877	Intermediate Similarity	NPC474246
0.7875	Intermediate Similarity	NPC477833
0.7875	Intermediate Similarity	NPC246647
0.7875	Intermediate Similarity	NPC217602
0.7875	Intermediate Similarity	NPC260902
0.7875	Intermediate Similarity	NPC104380
0.7875	Intermediate Similarity	NPC212967
0.7875	Intermediate Similarity	NPC296957
0.7875	Intermediate Similarity	NPC96342
0.7875	Intermediate Similarity	NPC473282
0.7875	Intermediate Similarity	NPC476404
0.7875	Intermediate Similarity	NPC164110
0.7875	Intermediate Similarity	NPC317900
0.7875	Intermediate Similarity	NPC294300
0.7872	Intermediate Similarity	NPC49441
0.7871	Intermediate Similarity	NPC46941
0.7871	Intermediate Similarity	NPC92054
0.7871	Intermediate Similarity	NPC202494
0.7871	Intermediate Similarity	NPC140722
0.7871	Intermediate Similarity	NPC4958
0.7867	Intermediate Similarity	NPC233707
0.7866	Intermediate Similarity	NPC119589
0.7862	Intermediate Similarity	NPC37392
0.7862	Intermediate Similarity	NPC104736
0.7862	Intermediate Similarity	NPC198490
0.7862	Intermediate Similarity	NPC59654
0.7862	Intermediate Similarity	NPC271832
0.7862	Intermediate Similarity	NPC175192
0.7857	Intermediate Similarity	NPC470857
0.7853	Intermediate Similarity	NPC133065
0.7853	Intermediate Similarity	NPC475985
0.7848	Intermediate Similarity	NPC207624
0.7848	Intermediate Similarity	NPC477957
0.7848	Intermediate Similarity	NPC44606
0.7848	Intermediate Similarity	NPC285623
0.7848	Intermediate Similarity	NPC215811
0.7848	Intermediate Similarity	NPC253872
0.7848	Intermediate Similarity	NPC67654

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 NPC469642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	911
0.2-0.3	1649
0.3-0.4	2667
0.4-0.5	1904
0.5-0.6	1173
0.6-0.7	449
0.7-0.8	90
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7952	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7748	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD1934	Approved
0.7593	Intermediate Similarity	NPD3882	Suspended
0.7578	Intermediate Similarity	NPD2801	Approved
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2935	Discontinued
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5402	Approved
0.7517	Intermediate Similarity	NPD6696	Suspended
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD5494	Approved
0.745	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3226	Approved
0.7414	Intermediate Similarity	NPD8434	Phase 2
0.7405	Intermediate Similarity	NPD2533	Approved
0.7405	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2534	Approved
0.7405	Intermediate Similarity	NPD2532	Approved
0.7403	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7396	Intermediate Similarity	NPD3818	Discontinued
0.7391	Intermediate Similarity	NPD4380	Phase 2
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD1607	Approved
0.7365	Intermediate Similarity	NPD2861	Phase 2
0.7361	Intermediate Similarity	NPD3496	Discontinued
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7338	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2309	Approved
0.7312	Intermediate Similarity	NPD920	Approved
0.731	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD6671	Approved
0.7303	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1778	Approved
0.729	Intermediate Similarity	NPD6004	Phase 3
0.729	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6002	Phase 3
0.7289	Intermediate Similarity	NPD919	Approved
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7261	Intermediate Similarity	NPD3750	Approved
0.7256	Intermediate Similarity	NPD5761	Phase 2
0.7256	Intermediate Similarity	NPD5760	Phase 2
0.7256	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9494	Approved
0.7237	Intermediate Similarity	NPD1240	Approved
0.7233	Intermediate Similarity	NPD1511	Approved
0.7233	Intermediate Similarity	NPD6799	Approved
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD411	Approved
0.7212	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5403	Approved
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7193	Intermediate Similarity	NPD2163	Approved
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2799	Discontinued
0.7161	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7126	Intermediate Similarity	NPD6765	Approved
0.7126	Intermediate Similarity	NPD6764	Approved
0.7126	Intermediate Similarity	NPD3749	Approved
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7114	Intermediate Similarity	NPD1203	Approved
0.711	Intermediate Similarity	NPD7074	Phase 3
0.7108	Intermediate Similarity	NPD3817	Phase 2
0.7108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD4749	Approved
0.7091	Intermediate Similarity	NPD6801	Discontinued
0.7089	Intermediate Similarity	NPD1243	Approved
0.7089	Intermediate Similarity	NPD2800	Approved
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD5401	Approved
0.7078	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2798	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7054	Approved
0.7044	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1241	Discontinued
0.7039	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6273	Approved
0.7034	Intermediate Similarity	NPD9545	Approved
0.703	Intermediate Similarity	NPD7411	Suspended
0.7027	Intermediate Similarity	NPD3972	Approved
0.7025	Intermediate Similarity	NPD2424	Discontinued
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3926	Phase 2
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7011	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2797	Approved
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4662	Approved
0.6975	Remote Similarity	NPD4661	Approved
0.6971	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6797	Phase 2
0.6968	Remote Similarity	NPD230	Phase 1
0.6966	Remote Similarity	NPD6785	Approved
0.6966	Remote Similarity	NPD6784	Approved
0.6964	Remote Similarity	NPD7768	Phase 2
0.6962	Remote Similarity	NPD1471	Phase 3
0.6959	Remote Similarity	NPD6232	Discontinued
0.6954	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3748	Approved
0.6939	Remote Similarity	NPD17	Approved
0.6936	Remote Similarity	NPD7473	Discontinued
0.6932	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7251	Discontinued
0.6928	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD6653	Approved
0.6913	Remote Similarity	NPD1481	Phase 2
0.6909	Remote Similarity	NPD2649	Approved
0.6909	Remote Similarity	NPD2651	Approved
0.6903	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4060	Phase 1
0.6903	Remote Similarity	NPD1613	Approved
0.6899	Remote Similarity	NPD6032	Approved
0.6897	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7177	Discontinued
0.6894	Remote Similarity	NPD3887	Approved
0.6893	Remote Similarity	NPD7808	Phase 3
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1470	Approved
0.6886	Remote Similarity	NPD37	Approved
0.6882	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5762	Approved
0.6855	Remote Similarity	NPD5763	Approved
0.6846	Remote Similarity	NPD1535	Discovery
0.6846	Remote Similarity	NPD1201	Approved
0.6845	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1465	Phase 2
0.6842	Remote Similarity	NPD5647	Approved
0.6842	Remote Similarity	NPD1019	Discontinued
0.6836	Remote Similarity	NPD7038	Approved
0.6836	Remote Similarity	NPD7039	Approved
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7003	Approved
0.6832	Remote Similarity	NPD4110	Phase 3
0.6829	Remote Similarity	NPD5049	Phase 3
0.6824	Remote Similarity	NPD4626	Approved
0.6821	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD3027	Phase 3
0.6806	Remote Similarity	NPD1398	Phase 1
0.6805	Remote Similarity	NPD2296	Approved
0.6802	Remote Similarity	NPD8127	Discontinued
0.68	Remote Similarity	NPD7228	Approved
0.68	Remote Similarity	NPD3751	Discontinued
0.6797	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6778	Approved
0.6791	Remote Similarity	NPD6782	Approved
0.6791	Remote Similarity	NPD6779	Approved
0.6791	Remote Similarity	NPD6781	Approved
0.6791	Remote Similarity	NPD6776	Approved
0.6791	Remote Similarity	NPD6777	Approved
0.6791	Remote Similarity	NPD6780	Approved
0.679	Remote Similarity	NPD6190	Approved
0.679	Remote Similarity	NPD2354	Approved
0.6788	Remote Similarity	NPD3869	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