NPASS Compound

Structure

NPC77807 OpenBabel07101719512D 24 26 0 0 0 0 0 0 0 0999 V2000 -5.1962 -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 -3.4641 -2.0000 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 -4.3301 -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 -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 -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 -4.3301 -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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 1 6 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	3.224
LogD:	2.467
LogS:	-4.065
# Rotatable Bonds:	2
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	3.098
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	1.2868151316069998e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.59021759033203%
Volume Distribution (VD):	0.453
Pgp-substrate:	8.147237777709961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.872
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.555
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	5.928
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.906
Carcinogencity:	0.281
Eye Corrosion:	0.008
Eye Irritation:	0.928
Respiratory Toxicity:	0.184

Download Data

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

Natural Product: NPC77807

Natural Product ID:	NPC77807
*Common Name:**	1,2,6-Trihydroxy-7,8-Dimethoxy-3-Methylanthraquinone
IUPAC Name:	1,2,6-trihydroxy-7,8-dimethoxy-3-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	VRTPFKPLZCEFKF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-6-4-7-10(15(22)12(6)19)14(21)11-8(13(7)20)5-9(18)16(23-2)17(11)24-3/h4-5,18-19,22H,1-3H3
SMILES:	Cc1cc2c(C(=O)c3c(cc(c(c3OC)OC)O)C2=O)c(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479128
PubChem CID:	11131324
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374975]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	100000.0	nM	PMID[518057]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100000.0	nM	PMID[518057]
NPT80	Cell Line	Raji	Homo sapiens	IC50	>	100000.0	nM	PMID[518057]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[518057]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[518057]
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	>	100000.0	nM	PMID[518057]

☑ 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 NPC77807 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	427
0.1-0.2	1896
0.2-0.3	4374
0.3-0.4	10914
0.4-0.5	7004
0.5-0.6	3402
0.6-0.7	5083
0.7-0.8	6049
0.8-0.85	2274
0.85-0.9	1136
0.9-0.95	122
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC14561
1.0	High Similarity	NPC5379
0.9933	High Similarity	NPC37543
0.9933	High Similarity	NPC178976
0.9933	High Similarity	NPC199463
0.9865	High Similarity	NPC107109
0.9801	High Similarity	NPC84571
0.9737	High Similarity	NPC311740
0.9664	High Similarity	NPC312338
0.9664	High Similarity	NPC149889
0.9597	High Similarity	NPC302783
0.9597	High Similarity	NPC473201
0.947	High Similarity	NPC93552
0.9467	High Similarity	NPC118427
0.9467	High Similarity	NPC78505
0.9459	High Similarity	NPC56433
0.9459	High Similarity	NPC312929
0.9459	High Similarity	NPC126767
0.9459	High Similarity	NPC190648
0.9459	High Similarity	NPC289042
0.9459	High Similarity	NPC245584
0.9459	High Similarity	NPC118027
0.9404	High Similarity	NPC164912
0.9367	High Similarity	NPC165979
0.9367	High Similarity	NPC163130
0.9351	High Similarity	NPC104876
0.9351	High Similarity	NPC245891
0.9333	High Similarity	NPC134293
0.9299	High Similarity	NPC26386
0.9295	High Similarity	NPC294965
0.9272	High Similarity	NPC294646
0.9272	High Similarity	NPC280295
0.9272	High Similarity	NPC470568
0.9272	High Similarity	NPC472279
0.9272	High Similarity	NPC147735
0.9272	High Similarity	NPC290954
0.9272	High Similarity	NPC255641
0.9257	High Similarity	NPC19896
0.925	High Similarity	NPC158226
0.9241	High Similarity	NPC29160
0.9236	High Similarity	NPC101769
0.9236	High Similarity	NPC270837
0.9236	High Similarity	NPC236132
0.9211	High Similarity	NPC470569
0.9211	High Similarity	NPC256406
0.9205	High Similarity	NPC264289
0.9205	High Similarity	NPC333691
0.9205	High Similarity	NPC142876
0.9205	High Similarity	NPC40290
0.9205	High Similarity	NPC139293
0.9205	High Similarity	NPC264550
0.9205	High Similarity	NPC69430
0.9205	High Similarity	NPC200060
0.9205	High Similarity	NPC195763
0.9195	High Similarity	NPC73416
0.9195	High Similarity	NPC160777
0.9182	High Similarity	NPC234331
0.9177	High Similarity	NPC303174
0.9167	High Similarity	NPC228785
0.9167	High Similarity	NPC56085
0.9167	High Similarity	NPC14353
0.9161	High Similarity	NPC136674
0.9156	High Similarity	NPC57674
0.9156	High Similarity	NPC234485
0.9156	High Similarity	NPC38898
0.9156	High Similarity	NPC39184
0.9156	High Similarity	NPC168247
0.9156	High Similarity	NPC230149
0.9156	High Similarity	NPC117992
0.9156	High Similarity	NPC134287
0.9156	High Similarity	NPC130589
0.9156	High Similarity	NPC152951
0.915	High Similarity	NPC40356
0.915	High Similarity	NPC154683
0.9145	High Similarity	NPC85131
0.9145	High Similarity	NPC151473
0.9139	High Similarity	NPC80710
0.9139	High Similarity	NPC254702
0.9139	High Similarity	NPC203747
0.9139	High Similarity	NPC166036
0.9139	High Similarity	NPC238279
0.9139	High Similarity	NPC139364
0.9139	High Similarity	NPC203077
0.9139	High Similarity	NPC194653
0.9128	High Similarity	NPC142165
0.9125	High Similarity	NPC49487
0.9125	High Similarity	NPC99613
0.9108	High Similarity	NPC278052
0.9108	High Similarity	NPC61010
0.9108	High Similarity	NPC66288
0.9108	High Similarity	NPC40491
0.9103	High Similarity	NPC235448
0.9103	High Similarity	NPC85121
0.9103	High Similarity	NPC477410
0.9103	High Similarity	NPC45846
0.9103	High Similarity	NPC100123
0.9097	High Similarity	NPC472455
0.9097	High Similarity	NPC279605
0.9091	High Similarity	NPC33051
0.9091	High Similarity	NPC49402
0.9091	High Similarity	NPC208806
0.9091	High Similarity	NPC227337
0.9091	High Similarity	NPC127172
0.9091	High Similarity	NPC273462
0.9091	High Similarity	NPC70433
0.9085	High Similarity	NPC144283
0.9085	High Similarity	NPC19980
0.9085	High Similarity	NPC45291
0.9079	High Similarity	NPC171916
0.9079	High Similarity	NPC38545
0.9073	High Similarity	NPC188074
0.9073	High Similarity	NPC125449
0.9073	High Similarity	NPC34802
0.9073	High Similarity	NPC77598
0.9067	High Similarity	NPC157133
0.906	High Similarity	NPC254659
0.906	High Similarity	NPC167663
0.906	High Similarity	NPC287722
0.9051	High Similarity	NPC470694
0.9045	High Similarity	NPC471973
0.9045	High Similarity	NPC320359
0.9045	High Similarity	NPC155302
0.9045	High Similarity	NPC161947
0.9045	High Similarity	NPC36217
0.9045	High Similarity	NPC119224
0.9038	High Similarity	NPC165977
0.9038	High Similarity	NPC262286
0.9038	High Similarity	NPC217677
0.9038	High Similarity	NPC36852
0.9038	High Similarity	NPC219867
0.9038	High Similarity	NPC161960
0.9038	High Similarity	NPC304008
0.9038	High Similarity	NPC472963
0.9038	High Similarity	NPC300727
0.9038	High Similarity	NPC241904
0.9038	High Similarity	NPC78103
0.9038	High Similarity	NPC180011
0.9038	High Similarity	NPC187745
0.9032	High Similarity	NPC234255
0.9032	High Similarity	NPC256925
0.9032	High Similarity	NPC226656
0.9032	High Similarity	NPC66508
0.9032	High Similarity	NPC472280
0.9032	High Similarity	NPC472048
0.9026	High Similarity	NPC474993
0.9026	High Similarity	NPC121522
0.9026	High Similarity	NPC181209
0.9026	High Similarity	NPC216769
0.9026	High Similarity	NPC100971
0.9026	High Similarity	NPC245382
0.9026	High Similarity	NPC269451
0.9026	High Similarity	NPC100263
0.9026	High Similarity	NPC291802
0.9026	High Similarity	NPC471982
0.9026	High Similarity	NPC209487
0.9026	High Similarity	NPC131266
0.9026	High Similarity	NPC35763
0.902	High Similarity	NPC29231
0.9018	High Similarity	NPC245975
0.9013	High Similarity	NPC183655
0.9013	High Similarity	NPC287395
0.9007	High Similarity	NPC12377
0.9	High Similarity	NPC207732
0.9	High Similarity	NPC193703
0.9	High Similarity	NPC105213
0.9	High Similarity	NPC37870
0.9	High Similarity	NPC21599
0.9	High Similarity	NPC43319
0.9	High Similarity	NPC48762
0.8994	High Similarity	NPC197168
0.8994	High Similarity	NPC236521
0.8994	High Similarity	NPC220313
0.8994	High Similarity	NPC152659
0.8994	High Similarity	NPC248638
0.8994	High Similarity	NPC7483
0.8993	High Similarity	NPC94076
0.8993	High Similarity	NPC284556
0.8993	High Similarity	NPC312256
0.8993	High Similarity	NPC301178
0.8993	High Similarity	NPC182255
0.8987	High Similarity	NPC87431
0.8981	High Similarity	NPC204879
0.8981	High Similarity	NPC476242
0.8974	High Similarity	NPC138243
0.8974	High Similarity	NPC6633
0.8974	High Similarity	NPC133970
0.8974	High Similarity	NPC474167
0.8974	High Similarity	NPC142339
0.8974	High Similarity	NPC470762
0.8974	High Similarity	NPC472907
0.8974	High Similarity	NPC274730
0.8974	High Similarity	NPC5322
0.8974	High Similarity	NPC115853
0.897	High Similarity	NPC212290
0.8968	High Similarity	NPC469550
0.8968	High Similarity	NPC214632
0.8968	High Similarity	NPC250557
0.8968	High Similarity	NPC124714
0.8968	High Similarity	NPC273248
0.8968	High Similarity	NPC472905

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 NPC77807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	1042
0.2-0.3	1736
0.3-0.4	2737
0.4-0.5	1699
0.5-0.6	977
0.6-0.7	378
0.7-0.8	142
0.8-0.85	29
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD6232	Discontinued
0.9119	High Similarity	NPD7473	Discontinued
0.8782	High Similarity	NPD1934	Approved
0.8726	High Similarity	NPD2393	Clinical (unspecified phase)
0.8726	High Similarity	NPD2801	Approved
0.8716	High Similarity	NPD1509	Clinical (unspecified phase)
0.8616	High Similarity	NPD3882	Suspended
0.8506	High Similarity	NPD1511	Approved
0.8456	Intermediate Similarity	NPD1607	Approved
0.8397	Intermediate Similarity	NPD1512	Approved
0.8364	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6166	Phase 2
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8322	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD943	Approved
0.8302	Intermediate Similarity	NPD4380	Phase 2
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8272	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD3818	Discontinued
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD2533	Approved
0.8217	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2534	Approved
0.8217	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3226	Approved
0.811	Intermediate Similarity	NPD7075	Discontinued
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3817	Phase 2
0.8065	Intermediate Similarity	NPD1549	Phase 2
0.8059	Intermediate Similarity	NPD7074	Phase 3
0.8057	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7390	Discontinued
0.8037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7953	Intermediate Similarity	NPD7472	Approved
0.7952	Intermediate Similarity	NPD6234	Discontinued
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3926	Phase 2
0.7866	Intermediate Similarity	NPD6801	Discontinued
0.7866	Intermediate Similarity	NPD37	Approved
0.7865	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1470	Approved
0.7848	Intermediate Similarity	NPD3750	Approved
0.7821	Intermediate Similarity	NPD2796	Approved
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6799	Approved
0.7803	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6797	Phase 2
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7785	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7759	Intermediate Similarity	NPD7251	Discontinued
0.7751	Intermediate Similarity	NPD1247	Approved
0.7738	Intermediate Similarity	NPD919	Approved
0.7725	Intermediate Similarity	NPD4967	Phase 2
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD4966	Approved
0.7725	Intermediate Similarity	NPD4965	Approved
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7808	Phase 3
0.7663	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD9494	Approved
0.763	Intermediate Similarity	NPD7228	Approved
0.7628	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8151	Discontinued
0.7602	Intermediate Similarity	NPD5710	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7595	Intermediate Similarity	NPD5408	Approved
0.7595	Intermediate Similarity	NPD5405	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7595	Intermediate Similarity	NPD5404	Approved
0.7595	Intermediate Similarity	NPD5406	Approved
0.7595	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1201	Approved
0.7568	Intermediate Similarity	NPD6781	Approved
0.7568	Intermediate Similarity	NPD6782	Approved
0.7568	Intermediate Similarity	NPD6776	Approved
0.7568	Intermediate Similarity	NPD6778	Approved
0.7568	Intermediate Similarity	NPD6779	Approved
0.7568	Intermediate Similarity	NPD6780	Approved
0.7568	Intermediate Similarity	NPD6777	Approved
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD3748	Approved
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8312	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.747	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5402	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD7435	Discontinued
0.7444	Intermediate Similarity	NPD8150	Discontinued
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7003	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1613	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.7354	Intermediate Similarity	NPD7698	Approved
0.7354	Intermediate Similarity	NPD7696	Phase 3
0.7354	Intermediate Similarity	NPD7697	Approved
0.7349	Intermediate Similarity	NPD5403	Approved
0.7349	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD5401	Approved
0.7316	Intermediate Similarity	NPD7870	Phase 2
0.7316	Intermediate Similarity	NPD7871	Phase 2
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7297	Intermediate Similarity	NPD6535	Approved
0.7297	Intermediate Similarity	NPD6534	Approved
0.7292	Intermediate Similarity	NPD7701	Phase 2
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD3764	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7238	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1933	Approved
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7216	Intermediate Similarity	NPD7874	Approved
0.7216	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6823	Phase 2
0.7208	Intermediate Similarity	NPD1283	Approved
0.72	Intermediate Similarity	NPD3787	Discontinued
0.7191	Intermediate Similarity	NPD7286	Phase 2
0.719	Intermediate Similarity	NPD3972	Approved
0.7181	Intermediate Similarity	NPD7700	Phase 2
0.7181	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD7801	Approved
0.7167	Intermediate Similarity	NPD7240	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD1651	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD1876	Approved
0.7091	Intermediate Similarity	NPD8166	Discontinued
0.7072	Intermediate Similarity	NPD7685	Pre-registration
0.7067	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD3620	Phase 2
0.7063	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6213	Phase 3
0.7059	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6212	Phase 3
0.7051	Intermediate Similarity	NPD1203	Approved
0.7047	Intermediate Similarity	NPD8319	Approved
0.7047	Intermediate Similarity	NPD8320	Phase 1
0.7039	Intermediate Similarity	NPD9268	Approved
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7037	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2654	Approved
0.7025	Intermediate Similarity	NPD4908	Phase 1
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7013	Intermediate Similarity	NPD1281	Approved
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD4626	Approved
0.6989	Remote Similarity	NPD4287	Approved
0.6962	Remote Similarity	NPD3018	Phase 2
0.6957	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD4288	Approved
0.6954	Remote Similarity	NPD5977	Approved

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