NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	343.11
LogP:	1.298
LogD:	1.469
LogS:	-4.111
# Rotatable Bonds:	1
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	3.635
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	1.102999613067368e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.296
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.539
Plasma Protein Binding (PPB):	73.701904296875%
Volume Distribution (VD):	0.768
Pgp-substrate:	9.737558364868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.399
CYP1A2-substrate:	0.649
CYP2C19-inhibitor:	0.433
CYP2C19-substrate:	0.519
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.707
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.309
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.654

ADMET: Excretion

Clearance (CL):	3.94
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.928
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.094
Carcinogencity:	0.572
Eye Corrosion:	0.003
Eye Irritation:	0.184
Respiratory Toxicity:	0.304

Download Data

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

Natural Product: NPC478018

Natural Product ID:	NPC478018
*Common Name:**	12-deoxo-12-hydroxy-8-O-methyltetrangomycin
IUPAC Name:	(3R)-3,12-dihydroxy-8-methoxy-3-methyl-4,12-dihydro-2H-benzo[a]anthracene-1,7-dione
Synonyms:
Standard InCHIKey:	YRKOFHPWOUTOGA-GFOWMXPYSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-20(24)8-10-6-7-12-17(15(10)13(21)9-20)19(23)11-4-3-5-14(25-2)16(11)18(12)22/h3-7,19,23-24H,8-9H2,1-2H3/t19?,20-/m1/s1
SMILES:	C[C@]1(CC2=C(C(=O)C1)C3=C(C=C2)C(=O)C4=C(C3O)C=CC=C4OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122195138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO33526	Streptomyces sp. CB01913	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26335269]

☑ 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	5
MIC	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	3100	nM	PMID[26335269]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	=	7200	nM	PMID[26335269]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	=	12000	nM	PMID[26335269]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	31000	nM	PMID[26335269]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	52000	nM	PMID[26335269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	PMID[26335269]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100	ug/ml	PMID[26335269]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	100	ug/ml	PMID[26335269]

☑ 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 NPC478018 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	365
0.1-0.2	1518
0.2-0.3	3204
0.3-0.4	8068
0.4-0.5	10612
0.5-0.6	4083
0.6-0.7	7047
0.7-0.8	6847
0.8-0.85	858
0.85-0.9	92
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC53016
0.9172	High Similarity	NPC478019
0.9097	High Similarity	NPC69755
0.902	High Similarity	NPC284495
0.8889	High Similarity	NPC470407
0.8873	High Similarity	NPC80035
0.8851	High Similarity	NPC300540
0.8844	High Similarity	NPC79627
0.8831	High Similarity	NPC324736
0.8824	High Similarity	NPC478223
0.8808	High Similarity	NPC470569
0.8767	High Similarity	NPC124365
0.8759	High Similarity	NPC1268
0.8759	High Similarity	NPC477408
0.8742	High Similarity	NPC147735
0.8742	High Similarity	NPC470568
0.8742	High Similarity	NPC290954
0.8742	High Similarity	NPC255641
0.8718	High Similarity	NPC472261
0.8693	High Similarity	NPC208806
0.869	High Similarity	NPC13715
0.8649	High Similarity	NPC66593
0.8649	High Similarity	NPC163948
0.8645	High Similarity	NPC10051
0.8645	High Similarity	NPC299094
0.8636	High Similarity	NPC66508
0.8636	High Similarity	NPC226656
0.8636	High Similarity	NPC318270
0.8627	High Similarity	NPC164912
0.8601	High Similarity	NPC470406
0.8601	High Similarity	NPC52407
0.86	High Similarity	NPC147250
0.86	High Similarity	NPC314437
0.8582	High Similarity	NPC57552
0.8581	High Similarity	NPC474861
0.8571	High Similarity	NPC179170
0.8571	High Similarity	NPC470841
0.8562	High Similarity	NPC234497
0.8562	High Similarity	NPC144283
0.8562	High Similarity	NPC105414
0.8562	High Similarity	NPC324522
0.8562	High Similarity	NPC470341
0.8562	High Similarity	NPC118427
0.8562	High Similarity	NPC472058
0.8553	High Similarity	NPC329933
0.8552	High Similarity	NPC141934
0.8544	High Similarity	NPC478229
0.8543	High Similarity	NPC312929
0.8543	High Similarity	NPC245584
0.8543	High Similarity	NPC126767
0.8543	High Similarity	NPC190648
0.8543	High Similarity	NPC289042
0.8543	High Similarity	NPC119767
0.8543	High Similarity	NPC34802
0.8543	High Similarity	NPC56433
0.8543	High Similarity	NPC118027
0.8542	High Similarity	NPC1249
0.8535	High Similarity	NPC476506
0.8533	High Similarity	NPC34482
0.8533	High Similarity	NPC49282
0.8526	High Similarity	NPC317580
0.8521	High Similarity	NPC199253
0.8521	High Similarity	NPC136588
0.8506	High Similarity	NPC40356
0.8506	High Similarity	NPC113608
0.8506	High Similarity	NPC470338
0.8506	High Similarity	NPC470340
0.8506	High Similarity	NPC154683
0.8506	High Similarity	NPC268992
0.8506	High Similarity	NPC470337
0.8506	High Similarity	NPC51824
0.8506	High Similarity	NPC180944
0.8497	Intermediate Similarity	NPC294646
0.8497	Intermediate Similarity	NPC315520
0.8487	Intermediate Similarity	NPC474107
0.8483	Intermediate Similarity	NPC22222
0.8483	Intermediate Similarity	NPC281513
0.8477	Intermediate Similarity	NPC143685
0.8477	Intermediate Similarity	NPC470570
0.8477	Intermediate Similarity	NPC285122
0.8472	Intermediate Similarity	NPC225051
0.8471	Intermediate Similarity	NPC326084
0.8467	Intermediate Similarity	NPC193703
0.8467	Intermediate Similarity	NPC21599
0.8467	Intermediate Similarity	NPC48762
0.8462	Intermediate Similarity	NPC221992
0.8462	Intermediate Similarity	NPC469507
0.8462	Intermediate Similarity	NPC474360
0.8456	Intermediate Similarity	NPC85310
0.8456	Intermediate Similarity	NPC469520
0.8456	Intermediate Similarity	NPC329493
0.8452	Intermediate Similarity	NPC214632
0.8452	Intermediate Similarity	NPC182921
0.8452	Intermediate Similarity	NPC218870
0.8452	Intermediate Similarity	NPC474621
0.8452	Intermediate Similarity	NPC474824
0.8452	Intermediate Similarity	NPC474622
0.8452	Intermediate Similarity	NPC470408
0.8452	Intermediate Similarity	NPC329844
0.8446	Intermediate Similarity	NPC315578
0.8442	Intermediate Similarity	NPC474417
0.8442	Intermediate Similarity	NPC145830
0.8442	Intermediate Similarity	NPC478148
0.8442	Intermediate Similarity	NPC149526
0.8442	Intermediate Similarity	NPC477276
0.8442	Intermediate Similarity	NPC473201
0.8442	Intermediate Similarity	NPC302783
0.8435	Intermediate Similarity	NPC475104
0.8431	Intermediate Similarity	NPC478219
0.8425	Intermediate Similarity	NPC155211
0.8421	Intermediate Similarity	NPC478163
0.8418	Intermediate Similarity	NPC470810
0.8418	Intermediate Similarity	NPC475449
0.8418	Intermediate Similarity	NPC472052
0.8418	Intermediate Similarity	NPC470342
0.8418	Intermediate Similarity	NPC472060
0.8414	Intermediate Similarity	NPC202225
0.8411	Intermediate Similarity	NPC73416
0.8411	Intermediate Similarity	NPC160777
0.8408	Intermediate Similarity	NPC67197
0.8408	Intermediate Similarity	NPC263483
0.8405	Intermediate Similarity	NPC473113
0.8403	Intermediate Similarity	NPC70622
0.8403	Intermediate Similarity	NPC183103
0.8403	Intermediate Similarity	NPC474340
0.84	Intermediate Similarity	NPC3732
0.84	Intermediate Similarity	NPC167663
0.8397	Intermediate Similarity	NPC68727
0.8397	Intermediate Similarity	NPC3898
0.8389	Intermediate Similarity	NPC149780
0.838	Intermediate Similarity	NPC48248
0.8378	Intermediate Similarity	NPC223336
0.8378	Intermediate Similarity	NPC26924
0.8377	Intermediate Similarity	NPC202595
0.8377	Intermediate Similarity	NPC225854
0.8377	Intermediate Similarity	NPC205766
0.8375	Intermediate Similarity	NPC476505
0.8367	Intermediate Similarity	NPC186647
0.8367	Intermediate Similarity	NPC301341
0.8367	Intermediate Similarity	NPC475957
0.8365	Intermediate Similarity	NPC18380
0.8365	Intermediate Similarity	NPC137232
0.8365	Intermediate Similarity	NPC478222
0.8365	Intermediate Similarity	NPC478134
0.8356	Intermediate Similarity	NPC22644
0.8354	Intermediate Similarity	NPC186113
0.8354	Intermediate Similarity	NPC472054
0.8345	Intermediate Similarity	NPC53896
0.8345	Intermediate Similarity	NPC115458
0.8345	Intermediate Similarity	NPC314048
0.8344	Intermediate Similarity	NPC117836
0.8344	Intermediate Similarity	NPC51887
0.8344	Intermediate Similarity	NPC279605
0.8344	Intermediate Similarity	NPC475705
0.8344	Intermediate Similarity	NPC19896
0.8344	Intermediate Similarity	NPC477409
0.8344	Intermediate Similarity	NPC478021
0.8344	Intermediate Similarity	NPC471451
0.8344	Intermediate Similarity	NPC476178
0.8333	Intermediate Similarity	NPC205360
0.8333	Intermediate Similarity	NPC474961
0.8333	Intermediate Similarity	NPC477412
0.8333	Intermediate Similarity	NPC135522
0.8333	Intermediate Similarity	NPC470087
0.8333	Intermediate Similarity	NPC49108
0.8333	Intermediate Similarity	NPC88958
0.8333	Intermediate Similarity	NPC155686
0.8333	Intermediate Similarity	NPC321980
0.8333	Intermediate Similarity	NPC164295
0.8333	Intermediate Similarity	NPC225419
0.8333	Intermediate Similarity	NPC210942
0.8333	Intermediate Similarity	NPC135524
0.8333	Intermediate Similarity	NPC169990
0.8323	Intermediate Similarity	NPC478022
0.8323	Intermediate Similarity	NPC46882
0.8323	Intermediate Similarity	NPC72958
0.8323	Intermediate Similarity	NPC469664
0.8323	Intermediate Similarity	NPC232645
0.8323	Intermediate Similarity	NPC476551
0.8323	Intermediate Similarity	NPC476552
0.8323	Intermediate Similarity	NPC478020
0.8323	Intermediate Similarity	NPC315221
0.8323	Intermediate Similarity	NPC472057
0.8323	Intermediate Similarity	NPC472051
0.8323	Intermediate Similarity	NPC132990
0.8323	Intermediate Similarity	NPC476553
0.8322	Intermediate Similarity	NPC473499
0.8313	Intermediate Similarity	NPC212099
0.8313	Intermediate Similarity	NPC278329
0.8313	Intermediate Similarity	NPC146837
0.8313	Intermediate Similarity	NPC101116
0.8313	Intermediate Similarity	NPC473961
0.8312	Intermediate Similarity	NPC65775
0.8312	Intermediate Similarity	NPC10027
0.8311	Intermediate Similarity	NPC4214
0.8303	Intermediate Similarity	NPC477991
0.8303	Intermediate Similarity	NPC477992
0.8302	Intermediate Similarity	NPC184326
0.8302	Intermediate Similarity	NPC472618
0.8302	Intermediate Similarity	NPC292863

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 NPC478018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	970
0.2-0.3	1357
0.3-0.4	2492
0.4-0.5	2090
0.5-0.6	1198
0.6-0.7	527
0.7-0.8	173
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD3226	Approved
0.8435	Intermediate Similarity	NPD2346	Discontinued
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8146	Intermediate Similarity	NPD7003	Approved
0.8121	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7458	Discontinued
0.8077	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD2799	Discontinued
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1470	Approved
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7885	Intermediate Similarity	NPD6273	Approved
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7390	Discontinued
0.7862	Intermediate Similarity	NPD2798	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7829	Intermediate Similarity	NPD1471	Phase 3
0.7824	Intermediate Similarity	NPD8312	Approved
0.7824	Intermediate Similarity	NPD8313	Approved
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD1510	Phase 2
0.7803	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5405	Approved
0.7763	Intermediate Similarity	NPD5408	Approved
0.7763	Intermediate Similarity	NPD5404	Approved
0.7763	Intermediate Similarity	NPD5406	Approved
0.7762	Intermediate Similarity	NPD1201	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7709	Intermediate Similarity	NPD6782	Approved
0.7709	Intermediate Similarity	NPD6778	Approved
0.7709	Intermediate Similarity	NPD6779	Approved
0.7709	Intermediate Similarity	NPD6781	Approved
0.7709	Intermediate Similarity	NPD6776	Approved
0.7709	Intermediate Similarity	NPD6777	Approved
0.7709	Intermediate Similarity	NPD6780	Approved
0.7708	Intermediate Similarity	NPD3972	Approved
0.7707	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD1651	Approved
0.7667	Intermediate Similarity	NPD1240	Approved
0.7662	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD2796	Approved
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5494	Approved
0.7603	Intermediate Similarity	NPD1283	Approved
0.7597	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6844	Discontinued
0.7593	Intermediate Similarity	NPD1934	Approved
0.7586	Intermediate Similarity	NPD8150	Discontinued
0.7582	Intermediate Similarity	NPD7698	Approved
0.7582	Intermediate Similarity	NPD7435	Discontinued
0.7582	Intermediate Similarity	NPD7696	Phase 3
0.7582	Intermediate Similarity	NPD7697	Approved
0.7574	Intermediate Similarity	NPD7177	Discontinued
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6166	Phase 2
0.756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7871	Phase 2
0.7541	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD3749	Approved
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4626	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2801	Approved
0.7436	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2979	Phase 3
0.7432	Intermediate Similarity	NPD6823	Phase 2
0.743	Intermediate Similarity	NPD6534	Approved
0.743	Intermediate Similarity	NPD6535	Approved
0.7419	Intermediate Similarity	NPD7701	Phase 2
0.7417	Intermediate Similarity	NPD3268	Approved
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7397	Intermediate Similarity	NPD1281	Approved
0.7394	Intermediate Similarity	NPD5402	Approved
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7365	Intermediate Similarity	NPD1876	Approved
0.7362	Intermediate Similarity	NPD6599	Discontinued
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7351	Intermediate Similarity	NPD7008	Discontinued
0.7349	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3882	Suspended
0.7343	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3750	Approved
0.734	Intermediate Similarity	NPD7874	Approved
0.734	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD5760	Phase 2
0.7333	Intermediate Similarity	NPD5761	Phase 2
0.7326	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1511	Approved
0.731	Intermediate Similarity	NPD5691	Approved
0.7308	Intermediate Similarity	NPD7700	Phase 2
0.7308	Intermediate Similarity	NPD7699	Phase 2
0.7303	Intermediate Similarity	NPD3764	Approved
0.7302	Intermediate Similarity	NPD7801	Approved
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7283	Intermediate Similarity	NPD7074	Phase 3
0.7278	Intermediate Similarity	NPD6212	Phase 3
0.7278	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6213	Phase 3
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3300	Phase 2
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7244	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7233	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD1512	Approved
0.7205	Intermediate Similarity	NPD6799	Approved
0.72	Intermediate Similarity	NPD1203	Approved
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7197	Intermediate Similarity	NPD1551	Phase 2
0.7197	Intermediate Similarity	NPD6099	Approved
0.7196	Intermediate Similarity	NPD8151	Discontinued
0.719	Intermediate Similarity	NPD411	Approved
0.7186	Intermediate Similarity	NPD3817	Phase 2
0.7184	Intermediate Similarity	NPD7472	Approved
0.7181	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5403	Approved
0.7174	Intermediate Similarity	NPD8285	Discontinued
0.717	Intermediate Similarity	NPD2800	Approved
0.7169	Intermediate Similarity	NPD37	Approved
0.7166	Intermediate Similarity	NPD8320	Phase 1
0.7166	Intermediate Similarity	NPD8319	Approved
0.7161	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD8166	Discontinued
0.7124	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9717	Approved
0.7108	Intermediate Similarity	NPD5890	Approved
0.7108	Intermediate Similarity	NPD5889	Approved
0.7105	Intermediate Similarity	NPD9494	Approved
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7097	Intermediate Similarity	NPD943	Approved
0.7091	Intermediate Similarity	NPD2651	Approved
0.7091	Intermediate Similarity	NPD2649	Approved
0.7089	Intermediate Similarity	NPD4477	Approved
0.7089	Intermediate Similarity	NPD2531	Phase 2
0.7089	Intermediate Similarity	NPD4476	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD3266	Approved
0.7083	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7076	Intermediate Similarity	NPD1247	Approved
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD920	Approved
0.7066	Intermediate Similarity	NPD7577	Discontinued
0.7063	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7062	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5401	Approved
0.7055	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD4661	Approved
0.7048	Intermediate Similarity	NPD6585	Discontinued
0.7045	Intermediate Similarity	NPD3823	Discontinued
0.7043	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4966	Approved
0.7041	Intermediate Similarity	NPD4967	Phase 2
0.7041	Intermediate Similarity	NPD4965	Approved
0.7035	Intermediate Similarity	NPD6808	Phase 2
0.7031	Intermediate Similarity	NPD7783	Phase 2
0.7031	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7239	Suspended
0.7027	Intermediate Similarity	NPD3019	Approved
0.7019	Intermediate Similarity	NPD6398	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