NPASS Compound

Structure

NPC470408 OpenBabel07101718242D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.9319 0.5176 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 -1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 1 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 1.7321 -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 3.4641 0.0000 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 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 32 1 0 0 0 0 3 7 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 1 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 6 0 0 0 18 26 2 0 0 0 0 19 27 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 32 1 0 0 0 0 23 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.13
Volume:	427.522
LogP:	4.47
LogD:	1.846
LogS:	-3.228
# Rotatable Bonds:	4
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.049
Fsp3:	0.304
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:	-5.599
MDCK Permeability:	5.4864831326995045e-06
Pgp-inhibitor:	0.032
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	96.58625030517578%
Volume Distribution (VD):	1.03
Pgp-substrate:	6.919801235198975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.517
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.736
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	3.1
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.741
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.712
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.748
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC470408

Natural Product ID:	NPC470408
*Common Name:**	Methyl (1R,2R,4S)-2,4,5,7,12-Pentahydroxy-6,11-Dioxo-2-Propyl-3,4-Dihydro-1H-Tetracene-1-Carboxylate
IUPAC Name:	methyl (1R,2R,4S)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-propyl-3,4-dihydro-1H-tetracene-1-carboxylate
Synonyms:
Standard InCHIKey:	RBVRMUUHLBHOCG-RLAVILMUSA-N
Standard InCHI:	InChI=1S/C23H22O9/c1-3-7-23(31)8-11(25)13-14(17(23)22(30)32-2)21(29)15-16(20(13)28)19(27)12-9(18(15)26)5-4-6-10(12)24/h4-6,11,17,24-25,28-29,31H,3,7-8H2,1-2H3/t11-,17-,23+/m0/s1
SMILES:	CCC[C@@]1(O)C[C@H](O)c2c([C@H]1C(=O)OC)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2024358
PubChem CID:	57381725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*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
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22250891]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25375258]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26444379]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27813411]
NPO32815	micromonospora sp.	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31794218]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6200.0	nM	PMID[556055]

☑ 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 NPC470408 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	343
0.1-0.2	1347
0.2-0.3	2828
0.3-0.4	6819
0.4-0.5	11503
0.5-0.6	5460
0.6-0.7	6755
0.7-0.8	6819
0.8-0.85	663
0.85-0.9	146
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474824
1.0	High Similarity	NPC182921
1.0	High Similarity	NPC218870
0.9865	High Similarity	NPC474861
0.9527	High Similarity	NPC315520
0.9161	High Similarity	NPC284495
0.915	High Similarity	NPC66029
0.9	High Similarity	NPC314437
0.8933	High Similarity	NPC471683
0.8889	High Similarity	NPC205766
0.8874	High Similarity	NPC285122
0.8859	High Similarity	NPC135524
0.8851	High Similarity	NPC315578
0.8816	High Similarity	NPC119767
0.8812	High Similarity	NPC478022
0.8812	High Similarity	NPC478020
0.8808	High Similarity	NPC170055
0.88	High Similarity	NPC471682
0.8792	High Similarity	NPC204045
0.8792	High Similarity	NPC305845
0.8784	High Similarity	NPC26924
0.8782	High Similarity	NPC3449
0.8758	High Similarity	NPC94781
0.875	High Similarity	NPC147250
0.8742	High Similarity	NPC300684
0.8742	High Similarity	NPC244691
0.8742	High Similarity	NPC471906
0.8742	High Similarity	NPC48130
0.8742	High Similarity	NPC84568
0.8742	High Similarity	NPC218866
0.8734	High Similarity	NPC324736
0.8733	High Similarity	NPC85310
0.8733	High Similarity	NPC474961
0.8733	High Similarity	NPC474300
0.8733	High Similarity	NPC469520
0.8733	High Similarity	NPC257644
0.8725	High Similarity	NPC169452
0.8725	High Similarity	NPC181560
0.8718	High Similarity	NPC474622
0.8718	High Similarity	NPC205172
0.8718	High Similarity	NPC209393
0.8718	High Similarity	NPC312482
0.8718	High Similarity	NPC474621
0.8701	High Similarity	NPC477221
0.8701	High Similarity	NPC44378
0.8701	High Similarity	NPC280753
0.8684	High Similarity	NPC34482
0.8675	High Similarity	NPC476473
0.8671	High Similarity	NPC208651
0.8671	High Similarity	NPC206641
0.8671	High Similarity	NPC317580
0.8667	High Similarity	NPC257003
0.8662	High Similarity	NPC192219
0.8662	High Similarity	NPC82190
0.8662	High Similarity	NPC318270
0.8662	High Similarity	NPC174599
0.8659	High Similarity	NPC477836
0.8658	High Similarity	NPC242994
0.8658	High Similarity	NPC143438
0.8658	High Similarity	NPC138099
0.8658	High Similarity	NPC190457
0.8654	High Similarity	NPC474533
0.8654	High Similarity	NPC474534
0.8649	High Similarity	NPC245923
0.8649	High Similarity	NPC305060
0.8636	High Similarity	NPC112816
0.8627	High Similarity	NPC470570
0.8627	High Similarity	NPC300540
0.8618	High Similarity	NPC48762
0.8618	High Similarity	NPC10764
0.8618	High Similarity	NPC193703
0.8618	High Similarity	NPC21599
0.8616	High Similarity	NPC326084
0.8609	High Similarity	NPC193555
0.8608	High Similarity	NPC148323
0.8608	High Similarity	NPC283480
0.8608	High Similarity	NPC478027
0.86	High Similarity	NPC37992
0.86	High Similarity	NPC32749
0.86	High Similarity	NPC220496
0.86	High Similarity	NPC147542
0.86	High Similarity	NPC327916
0.86	High Similarity	NPC42262
0.86	High Similarity	NPC241349
0.86	High Similarity	NPC225243
0.8598	High Similarity	NPC478021
0.8591	High Similarity	NPC4214
0.8591	High Similarity	NPC13715
0.859	High Similarity	NPC470569
0.859	High Similarity	NPC477276
0.8589	High Similarity	NPC107009
0.8589	High Similarity	NPC76647
0.8581	High Similarity	NPC272268
0.8581	High Similarity	NPC474813
0.8581	High Similarity	NPC120171
0.8581	High Similarity	NPC155211
0.858	High Similarity	NPC71390
0.8571	High Similarity	NPC290194
0.8571	High Similarity	NPC52161
0.8571	High Similarity	NPC187934
0.8571	High Similarity	NPC37709
0.8571	High Similarity	NPC315772
0.8571	High Similarity	NPC162751
0.8571	High Similarity	NPC97637
0.8562	High Similarity	NPC70622
0.8562	High Similarity	NPC475449
0.8553	High Similarity	NPC66593
0.8545	High Similarity	NPC473113
0.8545	High Similarity	NPC294501
0.8544	High Similarity	NPC314257
0.8544	High Similarity	NPC266469
0.8544	High Similarity	NPC66508
0.8544	High Similarity	NPC226656
0.8543	High Similarity	NPC106519
0.8543	High Similarity	NPC246638
0.8543	High Similarity	NPC187843
0.8543	High Similarity	NPC91019
0.8543	High Similarity	NPC290550
0.8533	High Similarity	NPC471602
0.8533	High Similarity	NPC256463
0.8533	High Similarity	NPC476477
0.8533	High Similarity	NPC306835
0.8533	High Similarity	NPC299405
0.8533	High Similarity	NPC216312
0.8533	High Similarity	NPC111422
0.8533	High Similarity	NPC29771
0.8528	High Similarity	NPC477835
0.8526	High Similarity	NPC470568
0.8526	High Similarity	NPC290954
0.8526	High Similarity	NPC255641
0.8526	High Similarity	NPC147735
0.8526	High Similarity	NPC294646
0.8523	High Similarity	NPC53414
0.8523	High Similarity	NPC53206
0.8523	High Similarity	NPC471905
0.8516	High Similarity	NPC106524
0.8516	High Similarity	NPC290695
0.8514	High Similarity	NPC161632
0.8514	High Similarity	NPC80035
0.8506	High Similarity	NPC136878
0.8503	High Similarity	NPC52407
0.8497	Intermediate Similarity	NPC79627
0.8493	Intermediate Similarity	NPC205992
0.8487	Intermediate Similarity	NPC239136
0.8487	Intermediate Similarity	NPC137649
0.8487	Intermediate Similarity	NPC19631
0.8477	Intermediate Similarity	NPC183345
0.8477	Intermediate Similarity	NPC168471
0.8476	Intermediate Similarity	NPC234497
0.8476	Intermediate Similarity	NPC472058
0.8476	Intermediate Similarity	NPC324522
0.8476	Intermediate Similarity	NPC105414
0.8476	Intermediate Similarity	NPC470341
0.8471	Intermediate Similarity	NPC205918
0.8456	Intermediate Similarity	NPC254847
0.8456	Intermediate Similarity	NPC118919
0.8452	Intermediate Similarity	NPC478018
0.8447	Intermediate Similarity	NPC476506
0.8447	Intermediate Similarity	NPC472055
0.8446	Intermediate Similarity	NPC288089
0.8442	Intermediate Similarity	NPC478019
0.8438	Intermediate Similarity	NPC263483
0.8435	Intermediate Similarity	NPC110609
0.8435	Intermediate Similarity	NPC242358
0.8435	Intermediate Similarity	NPC246693
0.8431	Intermediate Similarity	NPC174905
0.8431	Intermediate Similarity	NPC474203
0.8431	Intermediate Similarity	NPC451542
0.8431	Intermediate Similarity	NPC295712
0.8431	Intermediate Similarity	NPC296752
0.8431	Intermediate Similarity	NPC313047
0.8431	Intermediate Similarity	NPC293545
0.8428	Intermediate Similarity	NPC68727
0.8425	Intermediate Similarity	NPC199253
0.8425	Intermediate Similarity	NPC31799
0.8425	Intermediate Similarity	NPC136588
0.8421	Intermediate Similarity	NPC471444
0.8418	Intermediate Similarity	NPC478220
0.8415	Intermediate Similarity	NPC30027
0.8411	Intermediate Similarity	NPC295339
0.84	Intermediate Similarity	NPC62272
0.8397	Intermediate Similarity	NPC172329
0.8397	Intermediate Similarity	NPC142846
0.8397	Intermediate Similarity	NPC2569
0.8397	Intermediate Similarity	NPC470479
0.8395	Intermediate Similarity	NPC472261
0.8389	Intermediate Similarity	NPC283088
0.8387	Intermediate Similarity	NPC110882
0.8387	Intermediate Similarity	NPC63918
0.8387	Intermediate Similarity	NPC271944
0.8387	Intermediate Similarity	NPC143685
0.8387	Intermediate Similarity	NPC85393
0.8387	Intermediate Similarity	NPC120536
0.8385	Intermediate Similarity	NPC314795
0.8385	Intermediate Similarity	NPC470339
0.8385	Intermediate Similarity	NPC186113
0.8383	Intermediate Similarity	NPC472054
0.8378	Intermediate Similarity	NPC314048
0.8378	Intermediate Similarity	NPC225051
0.8378	Intermediate Similarity	NPC115458

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 NPC470408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	901
0.2-0.3	1575
0.3-0.4	2646
0.4-0.5	2154
0.5-0.6	1052
0.6-0.7	386
0.7-0.8	131
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.848	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD5404	Approved
0.84	Intermediate Similarity	NPD5408	Approved
0.84	Intermediate Similarity	NPD5406	Approved
0.84	Intermediate Similarity	NPD5405	Approved
0.8377	Intermediate Similarity	NPD7390	Discontinued
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8246	Intermediate Similarity	NPD8150	Discontinued
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD3226	Approved
0.8082	Intermediate Similarity	NPD1470	Approved
0.8068	Intermediate Similarity	NPD6534	Approved
0.8068	Intermediate Similarity	NPD6535	Approved
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8011	Intermediate Similarity	NPD7435	Discontinued
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6781	Approved
0.7944	Intermediate Similarity	NPD6779	Approved
0.7944	Intermediate Similarity	NPD6782	Approved
0.7944	Intermediate Similarity	NPD6780	Approved
0.7944	Intermediate Similarity	NPD6778	Approved
0.7944	Intermediate Similarity	NPD6777	Approved
0.7944	Intermediate Similarity	NPD6776	Approved
0.7933	Intermediate Similarity	NPD7700	Phase 2
0.7933	Intermediate Similarity	NPD7699	Phase 2
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7869	Intermediate Similarity	NPD8319	Approved
0.7869	Intermediate Similarity	NPD8320	Phase 1
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7861	Intermediate Similarity	NPD8313	Approved
0.7861	Intermediate Similarity	NPD8312	Approved
0.7841	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4380	Phase 2
0.7814	Intermediate Similarity	NPD7698	Approved
0.7814	Intermediate Similarity	NPD7696	Phase 3
0.7814	Intermediate Similarity	NPD7697	Approved
0.7808	Intermediate Similarity	NPD1201	Approved
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7772	Intermediate Similarity	NPD7870	Phase 2
0.7772	Intermediate Similarity	NPD7871	Phase 2
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7874	Approved
0.7709	Intermediate Similarity	NPD6212	Phase 3
0.7709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6213	Phase 3
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD7701	Phase 2
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7801	Approved
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5494	Approved
0.7568	Intermediate Similarity	NPD6823	Phase 2
0.7562	Intermediate Similarity	NPD6190	Approved
0.756	Intermediate Similarity	NPD3749	Approved
0.754	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD3764	Approved
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7443	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD3300	Phase 2
0.7401	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6166	Phase 2
0.7399	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3750	Approved
0.7391	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2801	Approved
0.7375	Intermediate Similarity	NPD1549	Phase 2
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1240	Approved
0.7368	Intermediate Similarity	NPD1164	Approved
0.736	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1934	Approved
0.7321	Intermediate Similarity	NPD37	Approved
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7314	Intermediate Similarity	NPD3818	Discontinued
0.7312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4628	Phase 3
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6273	Approved
0.7254	Intermediate Similarity	NPD7783	Phase 2
0.7254	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2796	Approved
0.725	Intermediate Similarity	NPD1551	Phase 2
0.7235	Intermediate Similarity	NPD3817	Phase 2
0.7232	Intermediate Similarity	NPD7074	Phase 3
0.7229	Intermediate Similarity	NPD5403	Approved
0.7216	Intermediate Similarity	NPD7177	Discontinued
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7191	Intermediate Similarity	NPD5953	Discontinued
0.7188	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD8166	Discontinued
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7135	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7111	Intermediate Similarity	NPD36	Approved
0.7111	Intermediate Similarity	NPD4954	Approved
0.7111	Intermediate Similarity	NPD5034	Approved
0.7111	Intermediate Similarity	NPD5026	Approved
0.7111	Intermediate Similarity	NPD5028	Approved
0.7111	Intermediate Similarity	NPD4955	Approved
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7108	Intermediate Similarity	NPD5401	Approved
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD6797	Phase 2
0.7093	Intermediate Similarity	NPD3882	Suspended
0.7091	Intermediate Similarity	NPD7236	Approved
0.7089	Intermediate Similarity	NPD6663	Approved
0.7083	Intermediate Similarity	NPD7239	Suspended
0.7081	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD1465	Phase 2
0.707	Intermediate Similarity	NPD7008	Discontinued
0.7056	Intermediate Similarity	NPD5030	Phase 2
0.7056	Intermediate Similarity	NPD7251	Discontinued
0.7051	Intermediate Similarity	NPD5736	Approved
0.7049	Intermediate Similarity	NPD5038	Approved
0.7049	Intermediate Similarity	NPD5037	Approved
0.7048	Intermediate Similarity	NPD1511	Approved
0.7047	Intermediate Similarity	NPD9493	Approved
0.7037	Intermediate Similarity	NPD6099	Approved
0.7037	Intermediate Similarity	NPD8285	Discontinued
0.7037	Intermediate Similarity	NPD6100	Approved
0.7027	Intermediate Similarity	NPD5951	Approved
0.7024	Intermediate Similarity	NPD920	Approved
0.7022	Intermediate Similarity	NPD7228	Approved
0.7017	Intermediate Similarity	NPD7808	Phase 3
0.701	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8059	Phase 3
0.6995	Remote Similarity	NPD5036	Approved
0.6989	Remote Similarity	NPD7229	Phase 3
0.6987	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD7286	Phase 2
0.6978	Remote Similarity	NPD5035	Approved
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6975	Remote Similarity	NPD7033	Discontinued
0.6974	Remote Similarity	NPD3019	Approved
0.697	Remote Similarity	NPD3400	Discontinued
0.6968	Remote Similarity	NPD1283	Approved
0.6964	Remote Similarity	NPD1512	Approved
0.6961	Remote Similarity	NPD5039	Approved
0.6959	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD9545	Approved
0.6936	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7799	Discontinued
0.6923	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2800	Approved
0.6905	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6832	Phase 2
0.6892	Remote Similarity	NPD7635	Approved
0.689	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2344	Approved
0.6882	Remote Similarity	NPD8360	Approved
0.6882	Remote Similarity	NPD8361	Approved
0.6871	Remote Similarity	NPD4308	Phase 3
0.6868	Remote Similarity	NPD7685	Pre-registration
0.6863	Remote Similarity	NPD2932	Approved
0.6863	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4956	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