NPASS Compound

Structure

NPC89664 OpenBabel07101719242D 25 26 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -3.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 2.5000 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 -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 0.0000 -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 1 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 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 0.0000 -0.0000 0.0000 C 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 24 1 0 0 0 0 5 7 1 0 0 0 0 5 10 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 11 20 2 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 7 1 1 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	351.717
LogP:	4.468
LogD:	2.933
LogS:	-3.421
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	3.187
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	2.105959902110044e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.314
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.33199310302734%
Volume Distribution (VD):	0.677
Pgp-substrate:	8.101771354675293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.35
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.765
CYP2D6-substrate:	0.755
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	2.865
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.588
AMES Toxicity:	0.445
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.935
Carcinogencity:	0.368
Eye Corrosion:	0.294
Eye Irritation:	0.946
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC89664

Natural Product ID:	NPC89664
*Common Name:**	5-O-Methyl-11-O-Acetylalkannin
IUPAC Name:	[(1S)-1-(8-hydroxy-5-methoxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
Synonyms:
Standard InCHIKey:	ZRTAPXYXXAPASQ-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C19H20O6/c1-10(2)5-7-15(25-11(3)20)12-9-14(22)17-16(24-4)8-6-13(21)18(17)19(12)23/h5-6,8-9,15,21H,7H2,1-4H3/t15-/m0/s1
SMILES:	COc1ccc(c2c1C(=O)C=C(C2=O)[C@@H](OC(=O)C)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097732
PubChem CID:	46833121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	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	14

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	620.0	nM	PMID[571048]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	90.0	nM	PMID[571048]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	780.0	nM	PMID[571048]
NPT2296	Cell Line	AU565	Homo sapiens	IC50	=	590.0	nM	PMID[571048]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	870.0	nM	PMID[571048]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	10990.0	nM	PMID[571048]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14070.0	nM	PMID[571048]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	660.0	nM	PMID[571048]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	440.0	nM	PMID[571048]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	7410.0	nM	PMID[571048]
NPT2405	Cell Line	SAOS-2	Homo sapiens	IC50	=	13810.0	nM	PMID[571048]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	590.0	nM	PMID[571048]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	660.0	nM	PMID[571048]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10190.0	nM	PMID[571048]

☑ 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 NPC89664 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	320
0.1-0.2	1337
0.2-0.3	3228
0.3-0.4	7244
0.4-0.5	11192
0.5-0.6	3938
0.6-0.7	6945
0.7-0.8	7631
0.8-0.85	751
0.85-0.9	84
0.9-0.95	8
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274085
0.9635	High Similarity	NPC216312
0.9635	High Similarity	NPC306835
0.9635	High Similarity	NPC111422
0.9635	High Similarity	NPC476477
0.9635	High Similarity	NPC29771
0.9635	High Similarity	NPC471602
0.9635	High Similarity	NPC256463
0.9635	High Similarity	NPC299405
0.9565	High Similarity	NPC241349
0.9565	High Similarity	NPC147542
0.9565	High Similarity	NPC327916
0.9565	High Similarity	NPC37992
0.9565	High Similarity	NPC42262
0.9565	High Similarity	NPC220496
0.9565	High Similarity	NPC32749
0.95	High Similarity	NPC476473
0.9496	High Similarity	NPC471444
0.9496	High Similarity	NPC257003
0.9429	High Similarity	NPC474300
0.9343	High Similarity	NPC281513
0.9343	High Similarity	NPC22222
0.9296	High Similarity	NPC477409
0.9214	High Similarity	NPC295339
0.9143	High Similarity	NPC61590
0.9028	High Similarity	NPC103910
0.8986	High Similarity	NPC242358
0.8986	High Similarity	NPC110609
0.8986	High Similarity	NPC246693
0.8958	High Similarity	NPC21873
0.8951	High Similarity	NPC124365
0.8944	High Similarity	NPC477408
0.8865	High Similarity	NPC141934
0.8839	High Similarity	NPC474301
0.8811	High Similarity	NPC1268
0.88	High Similarity	NPC281272
0.8776	High Similarity	NPC300540
0.8759	High Similarity	NPC45537
0.8759	High Similarity	NPC329493
0.875	High Similarity	NPC472050
0.8742	High Similarity	NPC477691
0.8733	High Similarity	NPC39819
0.8699	High Similarity	NPC472006
0.8693	High Similarity	NPC67197
0.8686	High Similarity	NPC306765
0.8675	High Similarity	NPC477690
0.8675	High Similarity	NPC180388
0.8667	High Similarity	NPC31132
0.8662	High Similarity	NPC27407
0.8658	High Similarity	NPC2569
0.8658	High Similarity	NPC172329
0.8658	High Similarity	NPC228012
0.8649	High Similarity	NPC107625
0.8649	High Similarity	NPC472033
0.8643	High Similarity	NPC205360
0.8611	High Similarity	NPC98395
0.8601	High Similarity	NPC232996
0.86	High Similarity	NPC70764
0.8591	High Similarity	NPC472036
0.8582	High Similarity	NPC477406
0.8582	High Similarity	NPC470160
0.8581	High Similarity	NPC474630
0.8581	High Similarity	NPC472034
0.8571	High Similarity	NPC51106
0.8562	High Similarity	NPC67650
0.8562	High Similarity	NPC1704
0.8562	High Similarity	NPC3898
0.8542	High Similarity	NPC471542
0.8533	High Similarity	NPC153417
0.8533	High Similarity	NPC5537
0.8531	High Similarity	NPC142027
0.8531	High Similarity	NPC298900
0.8526	High Similarity	NPC24761
0.8523	High Similarity	NPC211565
0.8523	High Similarity	NPC60389
0.8523	High Similarity	NPC147250
0.8516	High Similarity	NPC477692
0.8514	High Similarity	NPC475813
0.8514	High Similarity	NPC475201
0.8511	High Similarity	NPC7012
0.8511	High Similarity	NPC477412
0.8503	High Similarity	NPC474385
0.8497	Intermediate Similarity	NPC155686
0.8497	Intermediate Similarity	NPC135522
0.8497	Intermediate Similarity	NPC290927
0.8489	Intermediate Similarity	NPC71525
0.8489	Intermediate Similarity	NPC470841
0.8487	Intermediate Similarity	NPC46882
0.8487	Intermediate Similarity	NPC132990
0.8487	Intermediate Similarity	NPC70016
0.8487	Intermediate Similarity	NPC215921
0.8481	Intermediate Similarity	NPC178281
0.8467	Intermediate Similarity	NPC137296
0.8467	Intermediate Similarity	NPC119767
0.8467	Intermediate Similarity	NPC182646
0.8462	Intermediate Similarity	NPC1249
0.8462	Intermediate Similarity	NPC284495
0.8452	Intermediate Similarity	NPC263483
0.8452	Intermediate Similarity	NPC44199
0.8451	Intermediate Similarity	NPC118253
0.8446	Intermediate Similarity	NPC469542
0.8446	Intermediate Similarity	NPC215451
0.8446	Intermediate Similarity	NPC277369
0.8442	Intermediate Similarity	NPC99381
0.8435	Intermediate Similarity	NPC283292
0.8435	Intermediate Similarity	NPC149533
0.8435	Intermediate Similarity	NPC475730
0.8431	Intermediate Similarity	NPC474843
0.8431	Intermediate Similarity	NPC175978
0.8431	Intermediate Similarity	NPC470340
0.8425	Intermediate Similarity	NPC475045
0.8421	Intermediate Similarity	NPC470107
0.8421	Intermediate Similarity	NPC469670
0.8421	Intermediate Similarity	NPC470568
0.8421	Intermediate Similarity	NPC294646
0.8421	Intermediate Similarity	NPC469619
0.8421	Intermediate Similarity	NPC295036
0.8414	Intermediate Similarity	NPC301341
0.8414	Intermediate Similarity	NPC305060
0.8411	Intermediate Similarity	NPC215711
0.8411	Intermediate Similarity	NPC94781
0.8411	Intermediate Similarity	NPC73411
0.84	Intermediate Similarity	NPC225173
0.84	Intermediate Similarity	NPC308799
0.84	Intermediate Similarity	NPC163846
0.8397	Intermediate Similarity	NPC186113
0.8397	Intermediate Similarity	NPC470339
0.8392	Intermediate Similarity	NPC43627
0.8389	Intermediate Similarity	NPC86373
0.8389	Intermediate Similarity	NPC184702
0.8389	Intermediate Similarity	NPC42540
0.8389	Intermediate Similarity	NPC151607
0.8389	Intermediate Similarity	NPC280404
0.8389	Intermediate Similarity	NPC210425
0.8389	Intermediate Similarity	NPC277426
0.8387	Intermediate Similarity	NPC478223
0.838	Intermediate Similarity	NPC470831
0.838	Intermediate Similarity	NPC214702
0.8378	Intermediate Similarity	NPC469579
0.8378	Intermediate Similarity	NPC250755
0.8378	Intermediate Similarity	NPC49108
0.8367	Intermediate Similarity	NPC475063
0.8367	Intermediate Similarity	NPC477537
0.8367	Intermediate Similarity	NPC475044
0.8367	Intermediate Similarity	NPC315578
0.8366	Intermediate Similarity	NPC240768
0.8366	Intermediate Similarity	NPC470569
0.8366	Intermediate Similarity	NPC200773
0.8356	Intermediate Similarity	NPC197666
0.8356	Intermediate Similarity	NPC478200
0.8356	Intermediate Similarity	NPC475005
0.8356	Intermediate Similarity	NPC474943
0.8356	Intermediate Similarity	NPC191835
0.8356	Intermediate Similarity	NPC33144
0.8356	Intermediate Similarity	NPC126739
0.8356	Intermediate Similarity	NPC221104
0.8355	Intermediate Similarity	NPC270160
0.8355	Intermediate Similarity	NPC237440
0.8355	Intermediate Similarity	NPC73236
0.8355	Intermediate Similarity	NPC120171
0.8355	Intermediate Similarity	NPC4423
0.8355	Intermediate Similarity	NPC77325
0.8355	Intermediate Similarity	NPC44378
0.8355	Intermediate Similarity	NPC280753
0.8354	Intermediate Similarity	NPC146837
0.8354	Intermediate Similarity	NPC278329
0.8345	Intermediate Similarity	NPC291454
0.8344	Intermediate Similarity	NPC8817
0.8344	Intermediate Similarity	NPC71055
0.8344	Intermediate Similarity	NPC210320
0.8344	Intermediate Similarity	NPC143050
0.8344	Intermediate Similarity	NPC61284
0.8344	Intermediate Similarity	NPC313368
0.8344	Intermediate Similarity	NPC146884
0.8344	Intermediate Similarity	NPC472055
0.8344	Intermediate Similarity	NPC125801
0.8344	Intermediate Similarity	NPC113428
0.8333	Intermediate Similarity	NPC177742
0.8333	Intermediate Similarity	NPC477153
0.8333	Intermediate Similarity	NPC474309
0.8333	Intermediate Similarity	NPC474097
0.8333	Intermediate Similarity	NPC311339
0.8333	Intermediate Similarity	NPC29552
0.8333	Intermediate Similarity	NPC478019
0.8333	Intermediate Similarity	NPC27394
0.8333	Intermediate Similarity	NPC246466
0.8333	Intermediate Similarity	NPC475923
0.8333	Intermediate Similarity	NPC75694
0.8333	Intermediate Similarity	NPC477836
0.8323	Intermediate Similarity	NPC246274
0.8323	Intermediate Similarity	NPC237560
0.8323	Intermediate Similarity	NPC66029
0.8322	Intermediate Similarity	NPC477407
0.8322	Intermediate Similarity	NPC159721
0.8322	Intermediate Similarity	NPC469885
0.8322	Intermediate Similarity	NPC309430
0.8322	Intermediate Similarity	NPC471731
0.8322	Intermediate Similarity	NPC478202
0.8312	Intermediate Similarity	NPC40356
0.8312	Intermediate Similarity	NPC271681

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 NPC89664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	910
0.2-0.3	1561
0.3-0.4	2413
0.4-0.5	2032
0.5-0.6	1241
0.6-0.7	509
0.7-0.8	196
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.86	High Similarity	NPD3226	Approved
0.8542	High Similarity	NPD2935	Discontinued
0.8483	Intermediate Similarity	NPD2346	Discontinued
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8188	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD2799	Discontinued
0.8085	Intermediate Similarity	NPD1470	Approved
0.8056	Intermediate Similarity	NPD2313	Discontinued
0.8047	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD5402	Approved
0.7953	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3750	Approved
0.7931	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1551	Phase 2
0.7883	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8312	Approved
0.7857	Intermediate Similarity	NPD8313	Approved
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7829	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1201	Approved
0.7799	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2798	Approved
0.7771	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD447	Suspended
0.7764	Intermediate Similarity	NPD7075	Discontinued
0.7748	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD9717	Approved
0.7742	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1510	Phase 2
0.773	Intermediate Similarity	NPD6959	Discontinued
0.7722	Intermediate Similarity	NPD4380	Phase 2
0.7718	Intermediate Similarity	NPD1607	Approved
0.7708	Intermediate Similarity	NPD1203	Approved
0.7703	Intermediate Similarity	NPD1240	Approved
0.7702	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD1549	Phase 2
0.7688	Intermediate Similarity	NPD2801	Approved
0.7688	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD411	Approved
0.7687	Intermediate Similarity	NPD3764	Approved
0.7683	Intermediate Similarity	NPD5710	Approved
0.7683	Intermediate Similarity	NPD5711	Approved
0.7673	Intermediate Similarity	NPD7411	Suspended
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.766	Intermediate Similarity	NPD4626	Approved
0.7651	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9493	Approved
0.7625	Intermediate Similarity	NPD1934	Approved
0.7616	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD8150	Discontinued
0.761	Intermediate Similarity	NPD6599	Discontinued
0.7606	Intermediate Similarity	NPD3496	Discontinued
0.7597	Intermediate Similarity	NPD7003	Approved
0.7589	Intermediate Similarity	NPD5691	Approved
0.758	Intermediate Similarity	NPD6273	Approved
0.7566	Intermediate Similarity	NPD5404	Approved
0.7566	Intermediate Similarity	NPD5408	Approved
0.7566	Intermediate Similarity	NPD5406	Approved
0.7566	Intermediate Similarity	NPD2796	Approved
0.7566	Intermediate Similarity	NPD5405	Approved
0.7564	Intermediate Similarity	NPD6799	Approved
0.7561	Intermediate Similarity	NPD5494	Approved
0.7552	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3749	Approved
0.7532	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD2800	Approved
0.7531	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD6844	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7467	Intermediate Similarity	NPD2979	Phase 3
0.7444	Intermediate Similarity	NPD6780	Approved
0.7444	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD6776	Approved
0.7444	Intermediate Similarity	NPD6782	Approved
0.7444	Intermediate Similarity	NPD6781	Approved
0.7444	Intermediate Similarity	NPD6777	Approved
0.7444	Intermediate Similarity	NPD6779	Approved
0.7439	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2309	Approved
0.7423	Intermediate Similarity	NPD3817	Phase 2
0.7421	Intermediate Similarity	NPD920	Approved
0.7415	Intermediate Similarity	NPD1019	Discontinued
0.7413	Intermediate Similarity	NPD1778	Approved
0.7405	Intermediate Similarity	NPD5401	Approved
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7403	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6002	Phase 3
0.7403	Intermediate Similarity	NPD6005	Phase 3
0.7403	Intermediate Similarity	NPD6004	Phase 3
0.7403	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7177	Discontinued
0.7396	Intermediate Similarity	NPD3818	Discontinued
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7384	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5953	Discontinued
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7347	Intermediate Similarity	NPD2797	Approved
0.7342	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7322	Intermediate Similarity	NPD7697	Approved
0.7322	Intermediate Similarity	NPD7698	Approved
0.7322	Intermediate Similarity	NPD7696	Phase 3
0.731	Intermediate Similarity	NPD1611	Approved
0.731	Intermediate Similarity	NPD1281	Approved
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7301	Intermediate Similarity	NPD37	Approved
0.7299	Intermediate Similarity	NPD2182	Approved
0.7296	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7292	Intermediate Similarity	NPD17	Approved
0.729	Intermediate Similarity	NPD5762	Approved
0.729	Intermediate Similarity	NPD5763	Approved
0.7289	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD7870	Phase 2
0.7283	Intermediate Similarity	NPD7871	Phase 2
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7279	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD3300	Phase 2
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD4965	Approved
0.7273	Intermediate Similarity	NPD4967	Phase 2
0.7273	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7261	Intermediate Similarity	NPD8166	Discontinued
0.7257	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6651	Approved
0.7251	Intermediate Similarity	NPD7286	Phase 2
0.725	Intermediate Similarity	NPD1512	Approved
0.7248	Intermediate Similarity	NPD2861	Phase 2
0.7226	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD2438	Suspended
0.7226	Intermediate Similarity	NPD6099	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7219	Intermediate Similarity	NPD7985	Registered
0.7219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7197	Intermediate Similarity	NPD1243	Approved
0.7194	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6671	Approved
0.7181	Intermediate Similarity	NPD5647	Approved
0.717	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6534	Approved
0.7167	Intermediate Similarity	NPD6535	Approved
0.7166	Intermediate Similarity	NPD7701	Phase 2
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7125	Intermediate Similarity	NPD7390	Discontinued
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7117	Intermediate Similarity	NPD2649	Approved
0.7117	Intermediate Similarity	NPD2651	Approved
0.7115	Intermediate Similarity	NPD2531	Phase 2
0.7115	Intermediate Similarity	NPD6032	Approved
0.7114	Intermediate Similarity	NPD1164	Approved
0.7111	Intermediate Similarity	NPD6213	Phase 3
0.7111	Intermediate Similarity	NPD6212	Phase 3
0.7111	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7472	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD1247	Approved
0.7101	Intermediate Similarity	NPD8127	Discontinued
0.7083	Intermediate Similarity	NPD919	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