NPASS Compound

Structure

NPC474417 OpenBabel07101718282D 25 27 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 2.5981 -0.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 -1.5000 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 1.7321 0.0000 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 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 11 2 0 0 0 0 5 25 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	354.303
LogP:	4.533
LogD:	3.123
LogS:	-4.148
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	3.473
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.788
MDCK Permeability:	1.2153611351095606e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.108
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	96.5156021118164%
Volume Distribution (VD):	1.197
Pgp-substrate:	3.264072895050049%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.409
CYP2C19-inhibitor:	0.619
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.711
CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.401
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	15.238
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.655
AMES Toxicity:	0.285
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.7
Carcinogencity:	0.704
Eye Corrosion:	0.003
Eye Irritation:	0.18
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC474417

Natural Product ID:	NPC474417
*Common Name:**	Deacetylvismione H
IUPAC Name:	3,8,9-trihydroxy-3-methyl-6-(3-methylbut-2-enoxy)-2,4-dihydroanthracen-1-one
Synonyms:	Deacetylvismione H
Standard InCHIKey:	PAHWTMPJUWLVGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-11(2)4-5-25-14-7-12-6-13-9-20(3,24)10-16(22)18(13)19(23)17(12)15(21)8-14/h4,6-8,21,23-24H,5,9-10H2,1-3H3
SMILES:	CC(=CCOc1cc(O)c2c(c1)cc1c(c2O)C(=O)CC(C1)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467619
PubChem CID:	13940837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828475]
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.4	ug.mL-1	PMID[505373]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[505373]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[505373]

☑ 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 NPC474417 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	394
0.1-0.2	1632
0.2-0.3	3693
0.3-0.4	9541
0.4-0.5	9046
0.5-0.6	3492
0.6-0.7	5267
0.7-0.8	5345
0.8-0.85	2391
0.85-0.9	1525
0.9-0.95	351
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC149526
0.9862	High Similarity	NPC478148
0.9728	High Similarity	NPC210942
0.9728	High Similarity	NPC169990
0.9728	High Similarity	NPC329844
0.9726	High Similarity	NPC232645
0.9726	High Similarity	NPC72958
0.9724	High Similarity	NPC97029
0.9724	High Similarity	NPC100985
0.9724	High Similarity	NPC158338
0.9724	High Similarity	NPC288036
0.9724	High Similarity	NPC65589
0.9724	High Similarity	NPC97028
0.9722	High Similarity	NPC34802
0.966	High Similarity	NPC87708
0.966	High Similarity	NPC154683
0.966	High Similarity	NPC40356
0.9655	High Similarity	NPC7025
0.9655	High Similarity	NPC256672
0.9655	High Similarity	NPC27221
0.9589	High Similarity	NPC329933
0.9586	High Similarity	NPC7943
0.9586	High Similarity	NPC123202
0.9586	High Similarity	NPC22005
0.9444	High Similarity	NPC84266
0.9408	High Similarity	NPC470810
0.9404	High Similarity	NPC272196
0.9396	High Similarity	NPC217447
0.9392	High Similarity	NPC202595
0.9392	High Similarity	NPC470568
0.9392	High Similarity	NPC325983
0.9379	High Similarity	NPC189650
0.9375	High Similarity	NPC94076
0.9375	High Similarity	NPC182255
0.9329	High Similarity	NPC470569
0.9329	High Similarity	NPC258249
0.9324	High Similarity	NPC233267
0.9324	High Similarity	NPC65775
0.9324	High Similarity	NPC291049
0.9324	High Similarity	NPC10027
0.932	High Similarity	NPC190648
0.932	High Similarity	NPC118027
0.932	High Similarity	NPC289042
0.932	High Similarity	NPC56433
0.932	High Similarity	NPC312929
0.932	High Similarity	NPC126767
0.932	High Similarity	NPC245584
0.931	High Similarity	NPC310340
0.9281	High Similarity	NPC186325
0.9267	High Similarity	NPC273483
0.9262	High Similarity	NPC147735
0.9262	High Similarity	NPC290954
0.9262	High Similarity	NPC255641
0.9257	High Similarity	NPC105415
0.9252	High Similarity	NPC24136
0.9252	High Similarity	NPC290133
0.9252	High Similarity	NPC187282
0.9252	High Similarity	NPC196114
0.9221	High Similarity	NPC137232
0.9221	High Similarity	NPC189552
0.9221	High Similarity	NPC273467
0.9221	High Similarity	NPC18380
0.9216	High Similarity	NPC177650
0.9216	High Similarity	NPC85121
0.9216	High Similarity	NPC195167
0.9211	High Similarity	NPC146211
0.9211	High Similarity	NPC180924
0.9205	High Similarity	NPC472799
0.9205	High Similarity	NPC135522
0.9205	High Similarity	NPC214632
0.92	High Similarity	NPC133856
0.9195	High Similarity	NPC474052
0.9184	High Similarity	NPC271288
0.9172	High Similarity	NPC275734
0.9167	High Similarity	NPC469664
0.9161	High Similarity	NPC15374
0.9156	High Similarity	NPC292863
0.9156	High Similarity	NPC312993
0.9156	High Similarity	NPC184326
0.915	High Similarity	NPC164110
0.915	High Similarity	NPC212967
0.915	High Similarity	NPC246647
0.915	High Similarity	NPC44199
0.915	High Similarity	NPC96342
0.9145	High Similarity	NPC149618
0.9145	High Similarity	NPC66508
0.9145	High Similarity	NPC89625
0.9145	High Similarity	NPC226656
0.9133	High Similarity	NPC227122
0.9133	High Similarity	NPC294646
0.9133	High Similarity	NPC472633
0.9133	High Similarity	NPC150928
0.9133	High Similarity	NPC158866
0.9128	High Similarity	NPC37139
0.9128	High Similarity	NPC35150
0.9128	High Similarity	NPC106328
0.9122	High Similarity	NPC163846
0.9122	High Similarity	NPC470570
0.9122	High Similarity	NPC225173
0.9122	High Similarity	NPC473132
0.9122	High Similarity	NPC130176
0.9122	High Similarity	NPC473927
0.9122	High Similarity	NPC99454
0.9122	High Similarity	NPC477955
0.9122	High Similarity	NPC473135
0.9122	High Similarity	NPC470676
0.9116	High Similarity	NPC19896
0.9116	High Similarity	NPC316816
0.9116	High Similarity	NPC166138
0.9116	High Similarity	NPC214166
0.9116	High Similarity	NPC106985
0.9116	High Similarity	NPC18585
0.9116	High Similarity	NPC478086
0.911	High Similarity	NPC279650
0.911	High Similarity	NPC17170
0.911	High Similarity	NPC258630
0.911	High Similarity	NPC96408
0.911	High Similarity	NPC166689
0.911	High Similarity	NPC156190
0.9103	High Similarity	NPC197168
0.9097	High Similarity	NPC66288
0.9091	High Similarity	NPC474373
0.9091	High Similarity	NPC324736
0.9091	High Similarity	NPC55443
0.9091	High Similarity	NPC18699
0.9091	High Similarity	NPC472617
0.9085	High Similarity	NPC4547
0.9079	High Similarity	NPC95842
0.9079	High Similarity	NPC93552
0.9079	High Similarity	NPC280530
0.9079	High Similarity	NPC178964
0.9079	High Similarity	NPC208806
0.9079	High Similarity	NPC193200
0.9073	High Similarity	NPC305965
0.9067	High Similarity	NPC269420
0.9067	High Similarity	NPC473016
0.9067	High Similarity	NPC473978
0.906	High Similarity	NPC201731
0.906	High Similarity	NPC125801
0.906	High Similarity	NPC473077
0.906	High Similarity	NPC104406
0.906	High Similarity	NPC71055
0.906	High Similarity	NPC24673
0.906	High Similarity	NPC296998
0.906	High Similarity	NPC10990
0.906	High Similarity	NPC97716
0.906	High Similarity	NPC300988
0.906	High Similarity	NPC237635
0.906	High Similarity	NPC308200
0.906	High Similarity	NPC259632
0.906	High Similarity	NPC79469
0.9054	High Similarity	NPC209040
0.9054	High Similarity	NPC131579
0.9054	High Similarity	NPC470890
0.9054	High Similarity	NPC470673
0.9054	High Similarity	NPC34482
0.9054	High Similarity	NPC134621
0.9054	High Similarity	NPC311741
0.9054	High Similarity	NPC117716
0.9054	High Similarity	NPC49282
0.9054	High Similarity	NPC131568
0.9054	High Similarity	NPC470674
0.9054	High Similarity	NPC224714
0.9054	High Similarity	NPC234629
0.9048	High Similarity	NPC227579
0.9048	High Similarity	NPC296917
0.9048	High Similarity	NPC324436
0.9048	High Similarity	NPC194432
0.9048	High Similarity	NPC223500
0.9048	High Similarity	NPC144499
0.9048	High Similarity	NPC66515
0.9048	High Similarity	NPC37496
0.9048	High Similarity	NPC328164
0.9048	High Similarity	NPC182852
0.9048	High Similarity	NPC306829
0.9048	High Similarity	NPC228504
0.9048	High Similarity	NPC64915
0.9048	High Similarity	NPC125855
0.9048	High Similarity	NPC167663
0.9048	High Similarity	NPC324134
0.9048	High Similarity	NPC40833
0.9048	High Similarity	NPC166934
0.9048	High Similarity	NPC73028
0.9048	High Similarity	NPC161506
0.9048	High Similarity	NPC1089
0.9048	High Similarity	NPC148757
0.9048	High Similarity	NPC265040
0.9048	High Similarity	NPC167624
0.9048	High Similarity	NPC107572
0.9048	High Similarity	NPC220998
0.9048	High Similarity	NPC177354
0.9048	High Similarity	NPC78
0.9048	High Similarity	NPC166482
0.9048	High Similarity	NPC11561
0.9048	High Similarity	NPC32739
0.9048	High Similarity	NPC76372
0.9048	High Similarity	NPC10937
0.9048	High Similarity	NPC226636
0.9048	High Similarity	NPC76338
0.9045	High Similarity	NPC25361

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 NPC474417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	1005
0.2-0.3	1551
0.3-0.4	2575
0.4-0.5	1881
0.5-0.6	1097
0.6-0.7	462
0.7-0.8	168
0.8-0.85	38
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD6959	Discontinued
0.8954	High Similarity	NPD7819	Suspended
0.8926	High Similarity	NPD4378	Clinical (unspecified phase)
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8774	High Similarity	NPD8443	Clinical (unspecified phase)
0.8707	High Similarity	NPD1552	Clinical (unspecified phase)
0.8707	High Similarity	NPD1550	Clinical (unspecified phase)
0.8679	High Similarity	NPD6232	Discontinued
0.8675	High Similarity	NPD2534	Approved
0.8675	High Similarity	NPD2533	Approved
0.8675	High Similarity	NPD2532	Approved
0.8649	High Similarity	NPD1549	Phase 2
0.8634	High Similarity	NPD7473	Discontinued
0.8581	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD1509	Clinical (unspecified phase)
0.8562	High Similarity	NPD1607	Approved
0.8526	High Similarity	NPD1934	Approved
0.8523	High Similarity	NPD970	Clinical (unspecified phase)
0.8514	High Similarity	NPD2796	Approved
0.8487	Intermediate Similarity	NPD7390	Discontinued
0.8481	Intermediate Similarity	NPD7768	Phase 2
0.8457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7075	Discontinued
0.8428	Intermediate Similarity	NPD3749	Approved
0.8425	Intermediate Similarity	NPD1240	Approved
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8397	Intermediate Similarity	NPD4380	Phase 2
0.8389	Intermediate Similarity	NPD6100	Approved
0.8389	Intermediate Similarity	NPD6099	Approved
0.8366	Intermediate Similarity	NPD1511	Approved
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD3226	Approved
0.8289	Intermediate Similarity	NPD3750	Approved
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8258	Intermediate Similarity	NPD1512	Approved
0.825	Intermediate Similarity	NPD3882	Suspended
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8224	Intermediate Similarity	NPD2800	Approved
0.8224	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4625	Phase 3
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8146	Intermediate Similarity	NPD1551	Phase 2
0.8129	Intermediate Similarity	NPD6799	Approved
0.8098	Intermediate Similarity	NPD5494	Approved
0.8092	Intermediate Similarity	NPD2346	Discontinued
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5710	Approved
0.8	Intermediate Similarity	NPD5711	Approved
0.7987	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1243	Approved
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7929	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3818	Discontinued
0.7908	Intermediate Similarity	NPD5404	Approved
0.7908	Intermediate Similarity	NPD5406	Approved
0.7908	Intermediate Similarity	NPD5408	Approved
0.7908	Intermediate Similarity	NPD5405	Approved
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD920	Approved
0.7857	Intermediate Similarity	NPD2344	Approved
0.7848	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7472	Approved
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.7793	Intermediate Similarity	NPD1201	Approved
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7711	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD7003	Approved
0.7706	Intermediate Similarity	NPD7177	Discontinued
0.7703	Intermediate Similarity	NPD1470	Approved
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7687	Intermediate Similarity	NPD4749	Approved
0.7682	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7658	Intermediate Similarity	NPD2309	Approved
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD5403	Approved
0.7636	Intermediate Similarity	NPD5402	Approved
0.7633	Intermediate Similarity	NPD3926	Phase 2
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1247	Approved
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1651	Approved
0.7582	Intermediate Similarity	NPD943	Approved
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7546	Intermediate Similarity	NPD7458	Discontinued
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD6273	Approved
0.7467	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7451	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD3764	Approved
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4287	Approved
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7783	Phase 2
0.7421	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7697	Approved
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7417	Intermediate Similarity	NPD2798	Approved
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7405	Intermediate Similarity	NPD1471	Phase 3
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7383	Intermediate Similarity	NPD1608	Approved
0.7383	Intermediate Similarity	NPD3972	Approved
0.738	Intermediate Similarity	NPD7871	Phase 2
0.738	Intermediate Similarity	NPD7870	Phase 2
0.7365	Intermediate Similarity	NPD5760	Phase 2
0.7365	Intermediate Similarity	NPD5761	Phase 2
0.7355	Intermediate Similarity	NPD2979	Phase 3
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7351	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD411	Approved
0.7338	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4288	Approved
0.7315	Intermediate Similarity	NPD1281	Approved
0.7312	Intermediate Similarity	NPD2654	Approved
0.7312	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4626	Approved
0.7283	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD9717	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4307	Phase 2
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2438	Suspended
0.7233	Intermediate Similarity	NPD4476	Approved
0.7233	Intermediate Similarity	NPD4477	Approved
0.7232	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5691	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7216	Intermediate Similarity	NPD1729	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