NPASS Compound

Structure

CID34802 OpenBabel06191715362D 21 23 0 0 1 0 0 0 0 0999 V2000 3.5640 -1.2412 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 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 -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 2 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 1.7321 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 2.4676 -2.4914 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 2 21 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 5 12 2 0 0 0 0 6 9 1 0 0 0 0 6 16 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 15 2 0 0 0 0 15 19 1 0 0 0 0 16 1 1 6 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	2.715
LogD:	2.119
LogS:	-3.245
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	3.318
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
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:	9.124936696025543e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.07
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.219
30% Bioavailability (F30%):	0.313

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	92.00267028808594%
Volume Distribution (VD):	1.265
Pgp-substrate:	11.758563995361328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.406
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	14.946
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.637
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.213
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: NPC34802

Natural Product ID:	NPC34802
*Common Name:**	Asperflavin
IUPAC Name:	(3S)-3,6,9-trihydroxy-8-methoxy-3-methyl-2,4-dihydroanthracen-1-one
Synonyms:
Standard InCHIKey:	WCRDTBIKDNWXLR-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-16(20)6-9-3-8-4-10(17)5-12(21-2)14(8)15(19)13(9)11(18)7-16/h3-5,17,19-20H,6-7H2,1-2H3/t16-/m0/s1
SMILES:	COc1cc(O)cc2c1c(O)c1c(c2)C[C@](CC1=O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358707
PubChem CID:	14355112
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
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24606395]
NPO6417	Lecanora grumosa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4946	Antidesma venosum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7499	Mammillaria krameri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11458	Hymenoxys subintegra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6874	Desmodium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6189	Rhamnus nipalensis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10055	Stichoneuron caudatum	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8748	Dacrydium nidulum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1387	Lactarius violascens	Species	Russulaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25.0	ug.mL-1	PMID[532465]

☑ 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 NPC34802 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	403
0.1-0.2	1754
0.2-0.3	3915
0.3-0.4	10564
0.4-0.5	7852
0.5-0.6	3735
0.6-0.7	5498
0.7-0.8	5379
0.8-0.85	2295
0.85-0.9	1147
0.9-0.95	131
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC329933
0.9722	High Similarity	NPC474417
0.9722	High Similarity	NPC149526
0.9714	High Similarity	NPC84266
0.9643	High Similarity	NPC182255
0.9643	High Similarity	NPC94076
0.9589	High Similarity	NPC329844
0.9586	High Similarity	NPC478148
0.9583	High Similarity	NPC100985
0.9583	High Similarity	NPC65589
0.9583	High Similarity	NPC288036
0.9583	High Similarity	NPC97029
0.9583	High Similarity	NPC158338
0.9583	High Similarity	NPC97028
0.958	High Similarity	NPC56433
0.958	High Similarity	NPC289042
0.958	High Similarity	NPC118027
0.958	High Similarity	NPC312929
0.958	High Similarity	NPC190648
0.958	High Similarity	NPC126767
0.958	High Similarity	NPC245584
0.9517	High Similarity	NPC470568
0.9514	High Similarity	NPC27221
0.9514	High Similarity	NPC256672
0.9514	High Similarity	NPC7025
0.9456	High Similarity	NPC210942
0.9456	High Similarity	NPC169990
0.9452	High Similarity	NPC72958
0.9452	High Similarity	NPC470569
0.9452	High Similarity	NPC232645
0.9444	High Similarity	NPC22005
0.9444	High Similarity	NPC7943
0.9444	High Similarity	NPC123202
0.9392	High Similarity	NPC66508
0.9392	High Similarity	NPC226656
0.9388	High Similarity	NPC154683
0.9388	High Similarity	NPC40356
0.9388	High Similarity	NPC87708
0.9384	High Similarity	NPC147735
0.9384	High Similarity	NPC294646
0.9384	High Similarity	NPC255641
0.9384	High Similarity	NPC290954
0.9375	High Similarity	NPC163846
0.9375	High Similarity	NPC225173
0.9371	High Similarity	NPC19896
0.931	High Similarity	NPC125801
0.9301	High Similarity	NPC167663
0.9257	High Similarity	NPC217447
0.9252	High Similarity	NPC325983
0.9236	High Similarity	NPC189650
0.9231	High Similarity	NPC40118
0.9231	High Similarity	NPC49108
0.9231	High Similarity	NPC126534
0.9231	High Similarity	NPC232021
0.9225	High Similarity	NPC472366
0.9205	High Similarity	NPC324736
0.9195	High Similarity	NPC208806
0.9195	High Similarity	NPC107109
0.9195	High Similarity	NPC93552
0.9189	High Similarity	NPC258249
0.9184	High Similarity	NPC291049
0.9184	High Similarity	NPC233267
0.9184	High Similarity	NPC65775
0.9184	High Similarity	NPC10027
0.9172	High Similarity	NPC34482
0.9172	High Similarity	NPC49282
0.9167	High Similarity	NPC310340
0.9167	High Similarity	NPC297600
0.9161	High Similarity	NPC265178
0.9155	High Similarity	NPC251681
0.9155	High Similarity	NPC243528
0.9155	High Similarity	NPC21350
0.9145	High Similarity	NPC470810
0.9145	High Similarity	NPC472052
0.9145	High Similarity	NPC472060
0.9145	High Similarity	NPC186325
0.9145	High Similarity	NPC470342
0.9139	High Similarity	NPC37543
0.9139	High Similarity	NPC199463
0.9139	High Similarity	NPC272196
0.9128	High Similarity	NPC268992
0.9128	High Similarity	NPC113608
0.9128	High Similarity	NPC51824
0.9128	High Similarity	NPC470337
0.9128	High Similarity	NPC175978
0.9128	High Similarity	NPC470338
0.9122	High Similarity	NPC202595
0.9116	High Similarity	NPC472841
0.9116	High Similarity	NPC172329
0.9116	High Similarity	NPC2569
0.9116	High Similarity	NPC105415
0.911	High Similarity	NPC470570
0.911	High Similarity	NPC196114
0.9103	High Similarity	NPC193703
0.9103	High Similarity	NPC21599
0.9103	High Similarity	NPC48762
0.9097	High Similarity	NPC250755
0.9091	High Similarity	NPC109232
0.9091	High Similarity	NPC165172
0.9085	High Similarity	NPC317119
0.9085	High Similarity	NPC219686
0.9085	High Similarity	NPC273467
0.9085	High Similarity	NPC189552
0.9079	High Similarity	NPC228654
0.9079	High Similarity	NPC177650
0.9078	High Similarity	NPC191976
0.9078	High Similarity	NPC13575
0.9073	High Similarity	NPC14561
0.9073	High Similarity	NPC77807
0.9073	High Similarity	NPC5379
0.9073	High Similarity	NPC180924
0.9073	High Similarity	NPC146211
0.9073	High Similarity	NPC474360
0.9067	High Similarity	NPC214632
0.906	High Similarity	NPC133856
0.9054	High Similarity	NPC80370
0.9041	High Similarity	NPC478019
0.9034	High Similarity	NPC163948
0.9028	High Similarity	NPC253822
0.9028	High Similarity	NPC259166
0.9028	High Similarity	NPC172250
0.9028	High Similarity	NPC215311
0.9028	High Similarity	NPC204985
0.9028	High Similarity	NPC213659
0.9028	High Similarity	NPC144118
0.9028	High Similarity	NPC80962
0.9028	High Similarity	NPC48624
0.9028	High Similarity	NPC326109
0.9028	High Similarity	NPC219917
0.9028	High Similarity	NPC11056
0.9028	High Similarity	NPC275734
0.9021	High Similarity	NPC472368
0.902	High Similarity	NPC312993
0.9014	High Similarity	NPC98115
0.9014	High Similarity	NPC477242
0.9014	High Similarity	NPC41461
0.9014	High Similarity	NPC477244
0.9014	High Similarity	NPC477243
0.9014	High Similarity	NPC25287
0.9014	High Similarity	NPC1486
0.9014	High Similarity	NPC249606
0.9014	High Similarity	NPC150399
0.9014	High Similarity	NPC476333
0.9014	High Similarity	NPC12165
0.9014	High Similarity	NPC186838
0.9014	High Similarity	NPC473391
0.9014	High Similarity	NPC274109
0.9014	High Similarity	NPC168105
0.9014	High Similarity	NPC472364
0.9014	High Similarity	NPC66349
0.9014	High Similarity	NPC472367
0.9013	High Similarity	NPC263483
0.9013	High Similarity	NPC246647
0.9013	High Similarity	NPC178976
0.9013	High Similarity	NPC96342
0.9013	High Similarity	NPC164110
0.9013	High Similarity	NPC212967
0.9007	High Similarity	NPC103842
0.9007	High Similarity	NPC68727
0.9	High Similarity	NPC470340
0.9	High Similarity	NPC180944
0.9	High Similarity	NPC273483
0.9	High Similarity	NPC267205
0.8993	High Similarity	NPC227122
0.8993	High Similarity	NPC119929
0.8993	High Similarity	NPC158866
0.8993	High Similarity	NPC150928
0.8986	High Similarity	NPC37139
0.8986	High Similarity	NPC472056
0.898	High Similarity	NPC473132
0.898	High Similarity	NPC290133
0.898	High Similarity	NPC187282
0.898	High Similarity	NPC477955
0.898	High Similarity	NPC24136
0.898	High Similarity	NPC473927
0.898	High Similarity	NPC470676
0.898	High Similarity	NPC25844
0.898	High Similarity	NPC473135
0.8973	High Similarity	NPC106985
0.8973	High Similarity	NPC166138
0.8973	High Similarity	NPC18585
0.8966	High Similarity	NPC55832
0.8966	High Similarity	NPC26238
0.8966	High Similarity	NPC268204
0.8966	High Similarity	NPC52789
0.8966	High Similarity	NPC469404
0.8966	High Similarity	NPC26051
0.8961	High Similarity	NPC66288
0.8961	High Similarity	NPC137232
0.8961	High Similarity	NPC18380
0.8958	High Similarity	NPC295384
0.8958	High Similarity	NPC477956
0.8958	High Similarity	NPC283429
0.8958	High Similarity	NPC168471
0.8954	High Similarity	NPC85121
0.8954	High Similarity	NPC18699
0.8954	High Similarity	NPC195167
0.8954	High Similarity	NPC55443
0.8954	High Similarity	NPC474373
0.8951	High Similarity	NPC153979

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 NPC34802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1028
0.2-0.3	1514
0.3-0.4	2683
0.4-0.5	1869
0.5-0.6	1083
0.6-0.7	404
0.7-0.8	161
0.8-0.85	24
0.85-0.9	17
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD6959	Discontinued
0.8903	High Similarity	NPD6232	Discontinued
0.8854	High Similarity	NPD7473	Discontinued
0.8811	High Similarity	NPD1509	Clinical (unspecified phase)
0.8803	High Similarity	NPD1607	Approved
0.8784	High Similarity	NPD4378	Clinical (unspecified phase)
0.8716	High Similarity	NPD7390	Discontinued
0.8693	High Similarity	NPD7819	Suspended
0.8681	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD1240	Approved
0.8658	High Similarity	NPD2532	Approved
0.8658	High Similarity	NPD2533	Approved
0.8658	High Similarity	NPD2534	Approved
0.8658	High Similarity	NPD7410	Clinical (unspecified phase)
0.863	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.8516	High Similarity	NPD8443	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1549	Phase 2
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8291	Intermediate Similarity	NPD3749	Approved
0.8269	Intermediate Similarity	NPD1934	Approved
0.8243	Intermediate Similarity	NPD2796	Approved
0.8243	Intermediate Similarity	NPD6100	Approved
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8243	Intermediate Similarity	NPD6099	Approved
0.8228	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3226	Approved
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8163	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD3750	Approved
0.8121	Intermediate Similarity	NPD5405	Approved
0.8121	Intermediate Similarity	NPD5404	Approved
0.8121	Intermediate Similarity	NPD5408	Approved
0.8121	Intermediate Similarity	NPD5406	Approved
0.8117	Intermediate Similarity	NPD1512	Approved
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2800	Approved
0.8069	Intermediate Similarity	NPD4625	Phase 3
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8014	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5710	Approved
0.7975	Intermediate Similarity	NPD5711	Approved
0.7961	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2346	Discontinued
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD1470	Approved
0.7908	Intermediate Similarity	NPD7003	Approved
0.7908	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7871	Intermediate Similarity	NPD6799	Approved
0.7853	Intermediate Similarity	NPD5494	Approved
0.7843	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3817	Phase 2
0.7816	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3748	Approved
0.7801	Intermediate Similarity	NPD1651	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1283	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7707	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD7074	Phase 3
0.7679	Intermediate Similarity	NPD3818	Discontinued
0.7677	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7054	Approved
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD2798	Approved
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD920	Approved
0.76	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD7472	Approved
0.7586	Intermediate Similarity	NPD3972	Approved
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD7229	Phase 3
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7544	Intermediate Similarity	NPD6797	Phase 2
0.7534	Intermediate Similarity	NPD4749	Approved
0.7533	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD1281	Approved
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8151	Discontinued
0.7471	Intermediate Similarity	NPD7177	Discontinued
0.747	Intermediate Similarity	NPD919	Approved
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7808	Phase 3
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4965	Approved
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7417	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7394	Intermediate Similarity	NPD5402	Approved
0.7391	Intermediate Similarity	NPD7698	Approved
0.7391	Intermediate Similarity	NPD5403	Approved
0.7391	Intermediate Similarity	NPD7696	Phase 3
0.7391	Intermediate Similarity	NPD7435	Discontinued
0.7391	Intermediate Similarity	NPD7697	Approved
0.7386	Intermediate Similarity	NPD8150	Discontinued
0.7383	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7356	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7351	Intermediate Similarity	NPD7870	Phase 2
0.7351	Intermediate Similarity	NPD7871	Phase 2
0.7341	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2979	Phase 3
0.7315	Intermediate Similarity	NPD1203	Approved
0.7315	Intermediate Similarity	NPD1164	Approved
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD4287	Approved
0.7297	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD5401	Approved
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7248	Intermediate Similarity	NPD1876	Approved
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7243	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7238	Intermediate Similarity	NPD4360	Phase 2
0.7238	Intermediate Similarity	NPD4363	Phase 3
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.723	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7211	Intermediate Similarity	NPD7783	Phase 2
0.7211	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2797	Approved
0.7198	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4361	Phase 2
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5691	Approved
0.719	Intermediate Similarity	NPD411	Approved
0.7186	Intermediate Similarity	NPD4288	Approved
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7168	Intermediate Similarity	NPD7228	Approved
0.7162	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7874	Approved
0.7158	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7143	Intermediate Similarity	NPD3019	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7124	Intermediate Similarity	NPD3027	Phase 3
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7118	Intermediate Similarity	NPD6746	Phase 2
0.7115	Intermediate Similarity	NPD4097	Suspended
0.7114	Intermediate Similarity	NPD9717	Approved
0.7105	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9493	Approved
0.7103	Intermediate Similarity	NPD405	Clinical (unspecified phase)

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