NPASS Compound

Structure

NPC232387 OpenBabel07101719242D 24 26 0 0 0 0 0 0 0 0999 V2000 2.3802 -2.1828 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2924 2.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -1.6235 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 1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 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 -1.0000 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 2.1906 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 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 3.1906 -0.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5593 1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 10 19 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	342.876
LogP:	4.472
LogD:	3.393
LogS:	-6.337
# Rotatable Bonds:	3
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	2.448
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.206
MDCK Permeability:	3.659760841401294e-05
Pgp-inhibitor:	0.478
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.596
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	81.81122589111328%
Volume Distribution (VD):	0.592
Pgp-substrate:	9.053677558898926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.63
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.555
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.453
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	6.692
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.469
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.932
Carcinogencity:	0.16
Eye Corrosion:	0.016
Eye Irritation:	0.955
Respiratory Toxicity:	0.722

Download Data

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

Natural Product: NPC232387

Natural Product ID:	NPC232387
*Common Name:**	4,6,9-Trimethoxyphenanthropolone
IUPAC Name:	2,5,11-trimethoxy-3,8-dimethylcyclohepta[a]naphthalen-9-one
Synonyms:	4,6,9-Trimethoxyphenanthropolone
Standard InCHIKey:	DRHLTPUTOAKXAP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-11-6-13-8-18(23-4)14-7-12(2)17(22-3)9-15(14)20(13)19(24-5)10-16(11)21/h6-10H,1-5H3
SMILES:	Cc1cc2cc(c3cc(C)c(cc3c2c(cc1=O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078788
PubChem CID:	44557155
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[19778068]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23806014]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	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	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[514570]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	20.0	ug.mL-1	PMID[514570]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[514570]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[514570]
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[514570]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	20.0	ug.mL-1	PMID[514570]

☑ 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 NPC232387 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	459
0.1-0.2	1836
0.2-0.3	4293
0.3-0.4	11910
0.4-0.5	6286
0.5-0.6	4396
0.6-0.7	7629
0.7-0.8	5521
0.8-0.85	330
0.85-0.9	34
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC181675
0.8788	High Similarity	NPC290601
0.855	High Similarity	NPC183103
0.8516	High Similarity	NPC474737
0.8467	Intermediate Similarity	NPC201297
0.8456	Intermediate Similarity	NPC472523
0.8455	Intermediate Similarity	NPC25648
0.8443	Intermediate Similarity	NPC283169
0.8421	Intermediate Similarity	NPC1249
0.8417	Intermediate Similarity	NPC470723
0.8359	Intermediate Similarity	NPC75432
0.8346	Intermediate Similarity	NPC472524
0.8333	Intermediate Similarity	NPC239134
0.8333	Intermediate Similarity	NPC164295
0.8295	Intermediate Similarity	NPC105031
0.8273	Intermediate Similarity	NPC167663
0.8268	Intermediate Similarity	NPC251259
0.8258	Intermediate Similarity	NPC315769
0.8235	Intermediate Similarity	NPC186647
0.8231	Intermediate Similarity	NPC82299
0.8226	Intermediate Similarity	NPC312105
0.8214	Intermediate Similarity	NPC189650
0.8209	Intermediate Similarity	NPC470406
0.8195	Intermediate Similarity	NPC471983
0.8195	Intermediate Similarity	NPC191395
0.8195	Intermediate Similarity	NPC149337
0.8189	Intermediate Similarity	NPC129176
0.8189	Intermediate Similarity	NPC131868
0.8168	Intermediate Similarity	NPC428300
0.8168	Intermediate Similarity	NPC471986
0.8168	Intermediate Similarity	NPC473221
0.8156	Intermediate Similarity	NPC49282
0.8143	Intermediate Similarity	NPC84266
0.8134	Intermediate Similarity	NPC228843
0.8116	Intermediate Similarity	NPC470407
0.8116	Intermediate Similarity	NPC1268
0.8112	Intermediate Similarity	NPC472841
0.811	Intermediate Similarity	NPC103916
0.8106	Intermediate Similarity	NPC215300
0.8102	Intermediate Similarity	NPC470721
0.8102	Intermediate Similarity	NPC6100
0.8102	Intermediate Similarity	NPC156888
0.8102	Intermediate Similarity	NPC470722
0.8099	Intermediate Similarity	NPC473927
0.8092	Intermediate Similarity	NPC470724
0.8092	Intermediate Similarity	NPC170485
0.8088	Intermediate Similarity	NPC22644
0.8085	Intermediate Similarity	NPC260152
0.8085	Intermediate Similarity	NPC471305
0.8077	Intermediate Similarity	NPC56332
0.8071	Intermediate Similarity	NPC182255
0.8071	Intermediate Similarity	NPC94076
0.806	Intermediate Similarity	NPC282508
0.806	Intermediate Similarity	NPC301717
0.8047	Intermediate Similarity	NPC212559
0.8045	Intermediate Similarity	NPC57552
0.8043	Intermediate Similarity	NPC233707
0.8042	Intermediate Similarity	NPC34802
0.8033	Intermediate Similarity	NPC473809
0.803	Intermediate Similarity	NPC186889
0.803	Intermediate Similarity	NPC53781
0.8029	Intermediate Similarity	NPC471670
0.8015	Intermediate Similarity	NPC470726
0.8015	Intermediate Similarity	NPC213122
0.8015	Intermediate Similarity	NPC324117
0.8015	Intermediate Similarity	NPC209858
0.8014	Intermediate Similarity	NPC472840
0.8014	Intermediate Similarity	NPC36732
0.8	Intermediate Similarity	NPC165612
0.8	Intermediate Similarity	NPC312560
0.7985	Intermediate Similarity	NPC470725
0.7985	Intermediate Similarity	NPC470727
0.7984	Intermediate Similarity	NPC476633
0.7984	Intermediate Similarity	NPC35344
0.7984	Intermediate Similarity	NPC141003
0.7983	Intermediate Similarity	NPC241224
0.797	Intermediate Similarity	NPC38017
0.797	Intermediate Similarity	NPC223912
0.7958	Intermediate Similarity	NPC472836
0.7958	Intermediate Similarity	NPC86069
0.7956	Intermediate Similarity	NPC37410
0.7956	Intermediate Similarity	NPC152209
0.7955	Intermediate Similarity	NPC474264
0.7955	Intermediate Similarity	NPC101894
0.7955	Intermediate Similarity	NPC177925
0.7953	Intermediate Similarity	NPC63010
0.7945	Intermediate Similarity	NPC474414
0.7939	Intermediate Similarity	NPC228503
0.7939	Intermediate Similarity	NPC111088
0.7939	Intermediate Similarity	NPC138248
0.7931	Intermediate Similarity	NPC100985
0.7931	Intermediate Similarity	NPC97028
0.7931	Intermediate Similarity	NPC97029
0.7931	Intermediate Similarity	NPC158338
0.7931	Intermediate Similarity	NPC329933
0.7931	Intermediate Similarity	NPC80370
0.7931	Intermediate Similarity	NPC65589
0.7931	Intermediate Similarity	NPC288036
0.7926	Intermediate Similarity	NPC279596
0.7926	Intermediate Similarity	NPC160623
0.7923	Intermediate Similarity	NPC152946
0.7917	Intermediate Similarity	NPC56433
0.7917	Intermediate Similarity	NPC312929
0.7917	Intermediate Similarity	NPC245584
0.7917	Intermediate Similarity	NPC118027
0.7917	Intermediate Similarity	NPC126767
0.7917	Intermediate Similarity	NPC190648
0.7917	Intermediate Similarity	NPC289042
0.7914	Intermediate Similarity	NPC475104
0.7907	Intermediate Similarity	NPC102639
0.7907	Intermediate Similarity	NPC322569
0.7899	Intermediate Similarity	NPC170328
0.7899	Intermediate Similarity	NPC472648
0.7899	Intermediate Similarity	NPC206525
0.7899	Intermediate Similarity	NPC472649
0.7899	Intermediate Similarity	NPC141934
0.7899	Intermediate Similarity	NPC191462
0.7899	Intermediate Similarity	NPC471182
0.7899	Intermediate Similarity	NPC472647
0.7899	Intermediate Similarity	NPC133463
0.7895	Intermediate Similarity	NPC106511
0.7895	Intermediate Similarity	NPC21563
0.7891	Intermediate Similarity	NPC27615
0.7891	Intermediate Similarity	NPC98748
0.7887	Intermediate Similarity	NPC16353
0.7887	Intermediate Similarity	NPC50954
0.7887	Intermediate Similarity	NPC3732
0.7879	Intermediate Similarity	NPC278955
0.7879	Intermediate Similarity	NPC105718
0.7879	Intermediate Similarity	NPC293801
0.7879	Intermediate Similarity	NPC113495
0.7877	Intermediate Similarity	NPC474660
0.7877	Intermediate Similarity	NPC13282
0.7877	Intermediate Similarity	NPC470568
0.7874	Intermediate Similarity	NPC185738
0.7872	Intermediate Similarity	NPC124365
0.7868	Intermediate Similarity	NPC474340
0.7868	Intermediate Similarity	NPC19157
0.7862	Intermediate Similarity	NPC256672
0.7862	Intermediate Similarity	NPC472056
0.7862	Intermediate Similarity	NPC7025
0.7862	Intermediate Similarity	NPC27221
0.7852	Intermediate Similarity	NPC254000
0.7847	Intermediate Similarity	NPC225173
0.7847	Intermediate Similarity	NPC163846
0.7842	Intermediate Similarity	NPC71465
0.7842	Intermediate Similarity	NPC472646
0.7842	Intermediate Similarity	NPC56329
0.7842	Intermediate Similarity	NPC22902
0.7842	Intermediate Similarity	NPC266006
0.7842	Intermediate Similarity	NPC24394
0.7842	Intermediate Similarity	NPC242715
0.7836	Intermediate Similarity	NPC283114
0.7836	Intermediate Similarity	NPC149008
0.7836	Intermediate Similarity	NPC207702
0.7836	Intermediate Similarity	NPC125887
0.7836	Intermediate Similarity	NPC472968
0.7826	Intermediate Similarity	NPC35630
0.7826	Intermediate Similarity	NPC258780
0.7826	Intermediate Similarity	NPC89504
0.7826	Intermediate Similarity	NPC95485
0.7826	Intermediate Similarity	NPC88065
0.7823	Intermediate Similarity	NPC230848
0.7823	Intermediate Similarity	NPC72958
0.7823	Intermediate Similarity	NPC151537
0.7823	Intermediate Similarity	NPC232645
0.7823	Intermediate Similarity	NPC149526
0.7823	Intermediate Similarity	NPC474417
0.7823	Intermediate Similarity	NPC470569
0.7817	Intermediate Similarity	NPC49108
0.7815	Intermediate Similarity	NPC300166
0.781	Intermediate Similarity	NPC185777
0.781	Intermediate Similarity	NPC32778
0.7808	Intermediate Similarity	NPC300983
0.7803	Intermediate Similarity	NPC73413
0.7803	Intermediate Similarity	NPC201667
0.7801	Intermediate Similarity	NPC168471
0.7801	Intermediate Similarity	NPC472366
0.7794	Intermediate Similarity	NPC15543
0.7793	Intermediate Similarity	NPC125801
0.7793	Intermediate Similarity	NPC123202
0.7793	Intermediate Similarity	NPC7943
0.7793	Intermediate Similarity	NPC22005
0.7786	Intermediate Similarity	NPC132804
0.7786	Intermediate Similarity	NPC470962
0.7786	Intermediate Similarity	NPC220344
0.7786	Intermediate Similarity	NPC23870
0.7786	Intermediate Similarity	NPC243996
0.7786	Intermediate Similarity	NPC275061
0.7785	Intermediate Similarity	NPC66508
0.7785	Intermediate Similarity	NPC226656
0.7778	Intermediate Similarity	NPC16577
0.7778	Intermediate Similarity	NPC206028
0.777	Intermediate Similarity	NPC30632
0.777	Intermediate Similarity	NPC115861
0.777	Intermediate Similarity	NPC87708
0.777	Intermediate Similarity	NPC10429
0.777	Intermediate Similarity	NPC154683
0.777	Intermediate Similarity	NPC40356
0.777	Intermediate Similarity	NPC137125

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 NPC232387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1027
0.2-0.3	1432
0.3-0.4	2721
0.4-0.5	1903
0.5-0.6	1097
0.6-0.7	423
0.7-0.8	125
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD1651	Approved
0.8468	Intermediate Similarity	NPD5691	Approved
0.84	Intermediate Similarity	NPD4626	Approved
0.8125	Intermediate Similarity	NPD1281	Approved
0.7984	Intermediate Similarity	NPD1611	Approved
0.7939	Intermediate Similarity	NPD1283	Approved
0.7874	Intermediate Similarity	NPD5536	Phase 2
0.7868	Intermediate Similarity	NPD2979	Phase 3
0.7863	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3972	Approved
0.7778	Intermediate Similarity	NPD4625	Phase 3
0.7698	Intermediate Similarity	NPD5283	Phase 1
0.7669	Intermediate Similarity	NPD1876	Approved
0.7622	Intermediate Similarity	NPD7003	Approved
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7589	Intermediate Similarity	NPD2438	Suspended
0.7589	Intermediate Similarity	NPD2531	Phase 2
0.7552	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2346	Discontinued
0.7518	Intermediate Similarity	NPD3748	Approved
0.7518	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD7819	Suspended
0.7465	Intermediate Similarity	NPD2935	Discontinued
0.7463	Intermediate Similarity	NPD1669	Approved
0.7463	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3226	Approved
0.7431	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6696	Suspended
0.7376	Intermediate Similarity	NPD1607	Approved
0.7344	Intermediate Similarity	NPD5535	Approved
0.7343	Intermediate Similarity	NPD2796	Approved
0.7338	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5327	Phase 3
0.7313	Intermediate Similarity	NPD3705	Approved
0.7308	Intermediate Similarity	NPD709	Approved
0.7308	Intermediate Similarity	NPD6959	Discontinued
0.7299	Intermediate Similarity	NPD2798	Approved
0.7293	Intermediate Similarity	NPD17	Approved
0.7287	Intermediate Similarity	NPD1241	Discontinued
0.7286	Intermediate Similarity	NPD8032	Phase 2
0.728	Intermediate Similarity	NPD3134	Approved
0.7261	Intermediate Similarity	NPD6232	Discontinued
0.726	Intermediate Similarity	NPD3750	Approved
0.726	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4628	Phase 3
0.7254	Intermediate Similarity	NPD4097	Suspended
0.7246	Intermediate Similarity	NPD2861	Phase 2
0.7244	Intermediate Similarity	NPD5451	Approved
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7234	Intermediate Similarity	NPD1240	Approved
0.7233	Intermediate Similarity	NPD7473	Discontinued
0.7222	Intermediate Similarity	NPD4476	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD1358	Approved
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3443	Approved
0.7218	Intermediate Similarity	NPD3445	Approved
0.7218	Intermediate Similarity	NPD3444	Approved
0.7214	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7635	Approved
0.7206	Intermediate Similarity	NPD4749	Approved
0.7197	Intermediate Similarity	NPD7644	Approved
0.7194	Intermediate Similarity	NPD4908	Phase 1
0.7181	Intermediate Similarity	NPD2533	Approved
0.7181	Intermediate Similarity	NPD2534	Approved
0.7181	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2532	Approved
0.7176	Intermediate Similarity	NPD6387	Discontinued
0.7174	Intermediate Similarity	NPD4624	Approved
0.7172	Intermediate Similarity	NPD5763	Approved
0.7172	Intermediate Similarity	NPD5762	Approved
0.7164	Intermediate Similarity	NPD1778	Approved
0.7154	Intermediate Similarity	NPD495	Approved
0.7154	Intermediate Similarity	NPD498	Approved
0.7154	Intermediate Similarity	NPD496	Approved
0.7153	Intermediate Similarity	NPD1510	Phase 2
0.7153	Intermediate Similarity	NPD8651	Approved
0.7153	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1608	Approved
0.7124	Intermediate Similarity	NPD5090	Approved
0.7124	Intermediate Similarity	NPD5089	Approved
0.7123	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3018	Phase 2
0.7113	Intermediate Similarity	NPD4140	Approved
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD7458	Discontinued
0.7103	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD5405	Approved
0.7103	Intermediate Similarity	NPD5404	Approved
0.7103	Intermediate Similarity	NPD5406	Approved
0.7101	Intermediate Similarity	NPD1470	Approved
0.7101	Intermediate Similarity	NPD3266	Approved
0.7101	Intermediate Similarity	NPD3267	Approved
0.7099	Intermediate Similarity	NPD497	Approved
0.7092	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5109	Approved
0.7092	Intermediate Similarity	NPD5110	Phase 2
0.7092	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5111	Phase 2
0.709	Intermediate Similarity	NPD3025	Approved
0.709	Intermediate Similarity	NPD3024	Approved
0.709	Intermediate Similarity	NPD5585	Approved
0.7087	Intermediate Similarity	NPD2342	Discontinued
0.7075	Intermediate Similarity	NPD1243	Approved
0.7059	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1610	Phase 2
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7034	Intermediate Similarity	NPD4108	Discontinued
0.7032	Intermediate Similarity	NPD4585	Approved
0.7032	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5494	Approved
0.7023	Intermediate Similarity	NPD1398	Phase 1
0.7021	Intermediate Similarity	NPD7095	Approved
0.7021	Intermediate Similarity	NPD3027	Phase 3
0.702	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD2981	Phase 2
0.7	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD1139	Approved
0.7	Intermediate Similarity	NPD1137	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6992	Remote Similarity	NPD7340	Approved
0.6987	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3026	Approved
0.6985	Remote Similarity	NPD3023	Approved
0.6978	Remote Similarity	NPD2797	Approved
0.6975	Remote Similarity	NPD7177	Discontinued
0.6974	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2313	Discontinued
0.6972	Remote Similarity	NPD1296	Phase 2
0.6972	Remote Similarity	NPD3764	Approved
0.6972	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD6674	Discontinued
0.6957	Remote Similarity	NPD2982	Phase 2
0.6957	Remote Similarity	NPD2983	Phase 2
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6832	Phase 2
0.6948	Remote Similarity	NPD4380	Phase 2
0.6947	Remote Similarity	NPD1138	Approved
0.6944	Remote Similarity	NPD6355	Discontinued
0.6944	Remote Similarity	NPD3657	Discovery
0.6944	Remote Similarity	NPD5735	Approved
0.6943	Remote Similarity	NPD7768	Phase 2
0.6939	Remote Similarity	NPD2344	Approved
0.6939	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD422	Phase 1
0.6933	Remote Similarity	NPD6667	Approved
0.6933	Remote Similarity	NPD6666	Approved
0.6929	Remote Similarity	NPD9697	Approved
0.6923	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7157	Approved
0.6917	Remote Similarity	NPD6671	Approved
0.6912	Remote Similarity	NPD2932	Approved
0.6912	Remote Similarity	NPD3019	Approved
0.6908	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7411	Suspended
0.6899	Remote Similarity	NPD2684	Approved
0.6892	Remote Similarity	NPD2424	Discontinued
0.6892	Remote Similarity	NPD1549	Phase 2
0.6889	Remote Similarity	NPD1548	Phase 1
0.6887	Remote Similarity	NPD6799	Approved
0.6887	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2230	Approved
0.6884	Remote Similarity	NPD2232	Approved
0.6884	Remote Similarity	NPD2233	Approved
0.6879	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2237	Approved
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3620	Phase 2
0.6875	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD920	Approved
0.6855	Remote Similarity	NPD5709	Phase 3
0.6853	Remote Similarity	NPD6798	Discontinued
0.6853	Remote Similarity	NPD7985	Registered
0.6853	Remote Similarity	NPD7294	Phase 1
0.6846	Remote Similarity	NPD4750	Phase 3
0.6842	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4359	Approved
0.6835	Remote Similarity	NPD4967	Phase 2
0.6835	Remote Similarity	NPD4966	Approved
0.6835	Remote Similarity	NPD4965	Approved
0.6832	Remote Similarity	NPD7229	Phase 3
0.6831	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5124	Phase 1
0.6828	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1550	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