NPASS Compound

Structure

NPC474961 OpenBabel07101718292D 35 37 0 0 1 0 0 0 0 0999 V2000 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 1.7321 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 -0.0000 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 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 -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 0.0000 2.0000 0.0000 C 0 0 3 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 -1.0000 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 18 19 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 25 2 0 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 28 2 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 30 35 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.26
Volume:	519.353
LogP:	8.748
LogD:	3.87
LogS:	-2.506
# Rotatable Bonds:	6
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.145
Synthetic Accessibility Score:	3.516
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.112
MDCK Permeability:	9.754721759236418e-06
Pgp-inhibitor:	0.114
Pgp-substrate:	0.329
Human Intestinal Absorption (HIA):	0.537
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	83.92774200439453%
Volume Distribution (VD):	4.185
Pgp-substrate:	20.14108657836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.315
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.586
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	12.052
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.947
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.755
Respiratory Toxicity:	0.299

Download Data

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

Natural Product: NPC474961

Natural Product ID:	NPC474961
*Common Name:**	Kenganthranol B
IUPAC Name:	1,3,8,10-tetrahydroxy-6-methyl-2,4,5-tris(3-methylbut-2-enyl)-10H-anthracen-9-one
Synonyms:	kenganthranol B
Standard InCHIKey:	HAPSTBPDRQRBSO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H36O5/c1-15(2)8-11-19-18(7)14-22(31)25-23(19)29(34)24-20(12-9-16(3)4)27(32)21(13-10-17(5)6)28(33)26(24)30(25)35/h8-10,14,29,31-34H,11-13H2,1-7H3
SMILES:	CC(=CCc1c(O)c(CC=C(C)C)c(c2c1C(O)c1c(C2=O)c(O)cc(c1CC=C(C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490326
PubChem CID:	11496609
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
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[16499321]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17352491]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26727375]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	6300.0	nM	PMID[487705]

☑ 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 NPC474961 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	357
0.1-0.2	1358
0.2-0.3	3021
0.3-0.4	8157
0.4-0.5	11227
0.5-0.6	4589
0.6-0.7	6694
0.7-0.8	5727
0.8-0.85	1229
0.85-0.9	269
0.9-0.95	60
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC135524
0.9635	High Similarity	NPC305845
0.9635	High Similarity	NPC204045
0.9568	High Similarity	NPC471906
0.9568	High Similarity	NPC244691
0.9556	High Similarity	NPC191976
0.9489	High Similarity	NPC190457
0.9362	High Similarity	NPC34482
0.9348	High Similarity	NPC138099
0.9348	High Similarity	NPC242994
0.9343	High Similarity	NPC471905
0.9333	High Similarity	NPC267205
0.9296	High Similarity	NPC470570
0.9291	High Similarity	NPC48762
0.9281	High Similarity	NPC169452
0.9281	High Similarity	NPC181560
0.927	High Similarity	NPC254847
0.9236	High Similarity	NPC477221
0.9231	High Similarity	NPC290194
0.9209	High Similarity	NPC143438
0.9203	High Similarity	NPC53206
0.9203	High Similarity	NPC53414
0.9191	High Similarity	NPC314048
0.9155	High Similarity	NPC193703
0.9155	High Similarity	NPC21599
0.9149	High Similarity	NPC137649
0.9149	High Similarity	NPC193555
0.9124	High Similarity	NPC282780
0.9124	High Similarity	NPC166480
0.9116	High Similarity	NPC472211
0.9111	High Similarity	NPC147757
0.911	High Similarity	NPC470569
0.9078	High Similarity	NPC187843
0.9078	High Similarity	NPC246638
0.9065	High Similarity	NPC53001
0.9051	High Similarity	NPC213485
0.9051	High Similarity	NPC40524
0.9051	High Similarity	NPC139074
0.9041	High Similarity	NPC147735
0.9041	High Similarity	NPC470568
0.9028	High Similarity	NPC143685
0.9021	High Similarity	NPC227841
0.9014	High Similarity	NPC73061
0.9	High Similarity	NPC87723
0.8993	High Similarity	NPC118919
0.8986	High Similarity	NPC44437
0.8978	High Similarity	NPC478190
0.8971	High Similarity	NPC259942
0.8966	High Similarity	NPC37709
0.8951	High Similarity	NPC313047
0.8951	High Similarity	NPC295712
0.8951	High Similarity	NPC293545
0.8951	High Similarity	NPC474203
0.8951	High Similarity	NPC174905
0.8951	High Similarity	NPC451542
0.8944	High Similarity	NPC290550
0.8944	High Similarity	NPC110810
0.8921	High Similarity	NPC283590
0.8921	High Similarity	NPC249272
0.8921	High Similarity	NPC70859
0.8921	High Similarity	NPC61153
0.8921	High Similarity	NPC130899
0.8913	High Similarity	NPC37299
0.8913	High Similarity	NPC52407
0.8913	High Similarity	NPC180261
0.8912	High Similarity	NPC290954
0.8912	High Similarity	NPC255641
0.8905	High Similarity	NPC475042
0.8897	High Similarity	NPC92624
0.8889	High Similarity	NPC10764
0.8881	High Similarity	NPC85310
0.8851	High Similarity	NPC478148
0.8849	High Similarity	NPC474394
0.8849	High Similarity	NPC270899
0.8849	High Similarity	NPC12070
0.8849	High Similarity	NPC474519
0.8841	High Similarity	NPC70622
0.8841	High Similarity	NPC175738
0.8836	High Similarity	NPC126767
0.8836	High Similarity	NPC56433
0.8836	High Similarity	NPC190648
0.8836	High Similarity	NPC312929
0.8836	High Similarity	NPC245584
0.8836	High Similarity	NPC289042
0.8836	High Similarity	NPC118027
0.8836	High Similarity	NPC34802
0.8832	High Similarity	NPC62219
0.8828	High Similarity	NPC12402
0.8815	High Similarity	NPC473691
0.8811	High Similarity	NPC106519
0.8811	High Similarity	NPC91019
0.8803	High Similarity	NPC162939
0.8792	High Similarity	NPC470337
0.8792	High Similarity	NPC154683
0.8792	High Similarity	NPC470338
0.8792	High Similarity	NPC268992
0.8792	High Similarity	NPC51824
0.8792	High Similarity	NPC113608
0.8792	High Similarity	NPC40356
0.8786	High Similarity	NPC290803
0.8784	High Similarity	NPC202595
0.8784	High Similarity	NPC280295
0.8784	High Similarity	NPC294646
0.8777	High Similarity	NPC114183
0.8768	High Similarity	NPC93015
0.8767	High Similarity	NPC110882
0.8767	High Similarity	NPC271944
0.8767	High Similarity	NPC285122
0.8767	High Similarity	NPC85393
0.875	High Similarity	NPC469520
0.875	High Similarity	NPC324736
0.875	High Similarity	NPC116513
0.8741	High Similarity	NPC477454
0.8733	High Similarity	NPC474824
0.8733	High Similarity	NPC182921
0.8733	High Similarity	NPC218870
0.8733	High Similarity	NPC470408
0.8725	High Similarity	NPC232645
0.8725	High Similarity	NPC72958
0.8725	High Similarity	NPC149526
0.8725	High Similarity	NPC474417
0.8723	High Similarity	NPC315275
0.8716	High Similarity	NPC329933
0.8714	High Similarity	NPC202225
0.8699	High Similarity	NPC170055
0.8696	High Similarity	NPC199253
0.8696	High Similarity	NPC31799
0.8696	High Similarity	NPC136588
0.8693	High Similarity	NPC470810
0.869	High Similarity	NPC84266
0.869	High Similarity	NPC159721
0.869	High Similarity	NPC471731
0.869	High Similarity	NPC296752
0.8676	High Similarity	NPC267846
0.8675	High Similarity	NPC68727
0.8667	High Similarity	NPC87708
0.8667	High Similarity	NPC470340
0.8667	High Similarity	NPC152525
0.8667	High Similarity	NPC180944
0.8667	High Similarity	NPC68756
0.8662	High Similarity	NPC305060
0.8652	High Similarity	NPC283088
0.8652	High Similarity	NPC161632
0.8652	High Similarity	NPC278375
0.8649	High Similarity	NPC221352
0.8643	High Similarity	NPC48036
0.8639	High Similarity	NPC314437
0.8639	High Similarity	NPC136878
0.8633	High Similarity	NPC41847
0.8633	High Similarity	NPC471851
0.863	High Similarity	NPC218866
0.863	High Similarity	NPC300684
0.863	High Similarity	NPC151607
0.863	High Similarity	NPC84568
0.863	High Similarity	NPC48130
0.863	High Similarity	NPC42540
0.863	High Similarity	NPC19896
0.8627	High Similarity	NPC470559
0.8623	High Similarity	NPC474998
0.8623	High Similarity	NPC109123
0.8623	High Similarity	NPC99731
0.8621	High Similarity	NPC182255
0.8621	High Similarity	NPC471733
0.8621	High Similarity	NPC94076
0.8618	High Similarity	NPC474861
0.8613	High Similarity	NPC103356
0.8613	High Similarity	NPC72158
0.8613	High Similarity	NPC30501
0.8613	High Similarity	NPC23126
0.8613	High Similarity	NPC162612
0.8613	High Similarity	NPC190043
0.8613	High Similarity	NPC169250
0.8613	High Similarity	NPC105157
0.8613	High Similarity	NPC100067
0.8613	High Similarity	NPC266689
0.8613	High Similarity	NPC98254
0.8611	High Similarity	NPC183345
0.8611	High Similarity	NPC203063
0.8609	High Similarity	NPC208806
0.8609	High Similarity	NPC135522
0.8609	High Similarity	NPC193200
0.8609	High Similarity	NPC210942
0.8609	High Similarity	NPC169990
0.8603	High Similarity	NPC10926
0.8601	High Similarity	NPC4214
0.8601	High Similarity	NPC475974
0.8601	High Similarity	NPC13715
0.86	High Similarity	NPC35
0.8591	High Similarity	NPC97028
0.8591	High Similarity	NPC288036
0.8591	High Similarity	NPC65589
0.8591	High Similarity	NPC158338
0.8591	High Similarity	NPC97029
0.8591	High Similarity	NPC100985
0.8582	High Similarity	NPC475088
0.8581	High Similarity	NPC162751
0.8581	High Similarity	NPC315772
0.8581	High Similarity	NPC125801
0.8581	High Similarity	NPC52161
0.8571	High Similarity	NPC478019

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 NPC474961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	901
0.2-0.3	1548
0.3-0.4	2739
0.4-0.5	2107
0.5-0.6	1054
0.6-0.7	357
0.7-0.8	112
0.8-0.85	14
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.927	High Similarity	NPD1509	Clinical (unspecified phase)
0.9021	High Similarity	NPD7390	Discontinued
0.8397	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1470	Approved
0.8309	Intermediate Similarity	NPD1201	Approved
0.8302	Intermediate Similarity	NPD7473	Discontinued
0.8276	Intermediate Similarity	NPD5406	Approved
0.8276	Intermediate Similarity	NPD5405	Approved
0.8276	Intermediate Similarity	NPD5408	Approved
0.8276	Intermediate Similarity	NPD5404	Approved
0.8228	Intermediate Similarity	NPD6232	Discontinued
0.82	Intermediate Similarity	NPD2532	Approved
0.82	Intermediate Similarity	NPD2534	Approved
0.82	Intermediate Similarity	NPD2533	Approved
0.82	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD943	Approved
0.8129	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7819	Suspended
0.8079	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD4380	Phase 2
0.7959	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1510	Phase 2
0.7945	Intermediate Similarity	NPD1607	Approved
0.7852	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1934	Approved
0.7808	Intermediate Similarity	NPD1240	Approved
0.78	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1549	Phase 2
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.775	Intermediate Similarity	NPD7075	Discontinued
0.7727	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6166	Phase 2
0.7683	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2801	Approved
0.7667	Intermediate Similarity	NPD2796	Approved
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.7658	Intermediate Similarity	NPD7411	Suspended
0.7643	Intermediate Similarity	NPD3226	Approved
0.763	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8150	Discontinued
0.7578	Intermediate Similarity	NPD7768	Phase 2
0.7561	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD5710	Approved
0.7548	Intermediate Similarity	NPD1511	Approved
0.7546	Intermediate Similarity	NPD5494	Approved
0.7545	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7482	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3882	Suspended
0.7469	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6651	Approved
0.7452	Intermediate Similarity	NPD1512	Approved
0.7448	Intermediate Similarity	NPD1164	Approved
0.744	Intermediate Similarity	NPD7054	Approved
0.7434	Intermediate Similarity	NPD6100	Approved
0.7434	Intermediate Similarity	NPD6099	Approved
0.7423	Intermediate Similarity	NPD3749	Approved
0.7396	Intermediate Similarity	NPD7472	Approved
0.7394	Intermediate Similarity	NPD3019	Approved
0.7391	Intermediate Similarity	NPD37	Approved
0.7375	Intermediate Similarity	NPD6599	Discontinued
0.7372	Intermediate Similarity	NPD3300	Phase 2
0.7355	Intermediate Similarity	NPD3750	Approved
0.7345	Intermediate Similarity	NPD6534	Approved
0.7345	Intermediate Similarity	NPD6535	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7699	Phase 2
0.7318	Intermediate Similarity	NPD7700	Phase 2
0.7314	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7251	Discontinued
0.7301	Intermediate Similarity	NPD3817	Phase 2
0.7297	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD2932	Approved
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4965	Approved
0.7255	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6797	Phase 2
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9269	Phase 2
0.7238	Intermediate Similarity	NPD6777	Approved
0.7238	Intermediate Similarity	NPD6782	Approved
0.7238	Intermediate Similarity	NPD6780	Approved
0.7238	Intermediate Similarity	NPD6781	Approved
0.7238	Intermediate Similarity	NPD6776	Approved
0.7238	Intermediate Similarity	NPD6778	Approved
0.7238	Intermediate Similarity	NPD6779	Approved
0.7235	Intermediate Similarity	NPD6020	Phase 2
0.7226	Intermediate Similarity	NPD4750	Phase 3
0.7215	Intermediate Similarity	NPD6799	Approved
0.7213	Intermediate Similarity	NPD7698	Approved
0.7213	Intermediate Similarity	NPD7696	Phase 3
0.7213	Intermediate Similarity	NPD7435	Discontinued
0.7213	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD1551	Phase 2
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.7203	Intermediate Similarity	NPD9268	Approved
0.72	Intermediate Similarity	NPD3764	Approved
0.7195	Intermediate Similarity	NPD5402	Approved
0.7174	Intermediate Similarity	NPD7871	Phase 2
0.7174	Intermediate Similarity	NPD7870	Phase 2
0.7174	Intermediate Similarity	NPD8320	Phase 1
0.7174	Intermediate Similarity	NPD8319	Approved
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7168	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6663	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7134	Intermediate Similarity	NPD7003	Approved
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4628	Phase 3
0.7114	Intermediate Similarity	NPD5736	Approved
0.7095	Intermediate Similarity	NPD6213	Phase 3
0.7095	Intermediate Similarity	NPD6212	Phase 3
0.7095	Intermediate Similarity	NPD3094	Phase 2
0.7095	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6190	Approved
0.7086	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD920	Approved
0.7076	Intermediate Similarity	NPD7228	Approved
0.7071	Intermediate Similarity	NPD7635	Approved
0.7065	Intermediate Similarity	NPD6823	Phase 2
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7701	Phase 2
0.7052	Intermediate Similarity	NPD5953	Discontinued
0.7051	Intermediate Similarity	NPD2344	Approved
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3748	Approved
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7025	Intermediate Similarity	NPD3400	Discontinued
0.702	Intermediate Similarity	NPD4625	Phase 3
0.7014	Intermediate Similarity	NPD3091	Approved
0.6986	Remote Similarity	NPD3026	Approved
0.6986	Remote Similarity	NPD3023	Approved
0.6984	Remote Similarity	NPD7874	Approved
0.6984	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3751	Discontinued
0.6975	Remote Similarity	NPD5403	Approved
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2313	Discontinued
0.6972	Remote Similarity	NPD5951	Approved
0.6971	Remote Similarity	NPD5026	Approved
0.6971	Remote Similarity	NPD5034	Approved
0.6971	Remote Similarity	NPD4954	Approved
0.6971	Remote Similarity	NPD36	Approved
0.6971	Remote Similarity	NPD4955	Approved
0.6971	Remote Similarity	NPD5028	Approved
0.6966	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD3024	Approved
0.6966	Remote Similarity	NPD3025	Approved
0.6962	Remote Similarity	NPD1243	Approved
0.6961	Remote Similarity	NPD4363	Phase 3
0.6961	Remote Similarity	NPD4360	Phase 2
0.6957	Remote Similarity	NPD2342	Discontinued
0.6957	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7801	Approved
0.6947	Remote Similarity	NPD7783	Phase 2
0.6947	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3787	Discontinued
0.6939	Remote Similarity	NPD3092	Approved
0.6933	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5035	Approved
0.6928	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD5760	Phase 2
0.6918	Remote Similarity	NPD8166	Discontinued
0.6915	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD5030	Phase 2
0.6913	Remote Similarity	NPD1283	Approved
0.691	Remote Similarity	NPD5038	Approved
0.691	Remote Similarity	NPD5037	Approved
0.6892	Remote Similarity	NPD3972	Approved
0.6886	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1247	Approved
0.6875	Remote Similarity	NPD9493	Approved
0.6875	Remote Similarity	NPD2309	Approved
0.6871	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7211	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