NPASS Compound

Structure

CID85368 OpenBabel06191715422D 35 39 0 0 1 0 0 0 0 0999 V2000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 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 1.7321 -0.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 6.0000 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 6.0622 2.5000 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 4.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 33 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 11 2 1 1 0 0 0 11 20 1 0 0 0 0 11 34 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 35 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 29 2 0 0 0 0 22 30 1 0 0 0 0 23 31 2 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 34 1 0 0 0 0 26 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.14
Volume:	468.217
LogP:	4.543
LogD:	2.807
LogS:	-6.768
# Rotatable Bonds:	3
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	4.08
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.919
MDCK Permeability:	1.0753573405963834e-05
Pgp-inhibitor:	0.685
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.603
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	98.3682632446289%
Volume Distribution (VD):	0.566
Pgp-substrate:	2.005988121032715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.597
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.274
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	3.312
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.877
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.672
Carcinogencity:	0.856
Eye Corrosion:	0.003
Eye Irritation:	0.846
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC85368

Natural Product ID:	NPC85368
*Common Name:**	Tetracenoquinocin
IUPAC Name:	10-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-1,11-dihydroxy-8-methyltetracene-5,12-dione
Synonyms:	Tetracenoquinocin
Standard InCHIKey:	DDAFXQZMYKLUIV-XEOGOGAXSA-N
Standard InCHI:	InChI=1S/C26H24O9/c1-10-7-12-9-14-19(23(31)18-13(21(14)29)5-4-6-15(18)27)22(30)17(12)16(8-10)35-26-25(33-3)24(32)20(28)11(2)34-26/h4-9,11,20,24-28,30,32H,1-3H3/t11-,20-,24+,25+,26-/m0/s1
SMILES:	Cc1cc2cc3c(c(c2c(c1)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)OC)O)C(=O)c1c(cccc1O)C3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094937
PubChem CID:	46210465
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
NPO41053	Streptomyces sp. Sp080513GE-26	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20192240]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	120000.0	nM	PMID[545007]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	210000.0	nM	PMID[545007]

☑ 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 NPC85368 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	416
0.1-0.2	1602
0.2-0.3	3323
0.3-0.4	8264
0.4-0.5	9795
0.5-0.6	4848
0.6-0.7	5773
0.7-0.8	6312
0.8-0.85	1858
0.85-0.9	436
0.9-0.95	61
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC153578
0.9758	High Similarity	NPC114257
0.9758	High Similarity	NPC277710
0.9758	High Similarity	NPC299149
0.9755	High Similarity	NPC203751
0.9636	High Similarity	NPC102053
0.9636	High Similarity	NPC289876
0.9527	High Similarity	NPC87583
0.9521	High Similarity	NPC58538
0.9518	High Similarity	NPC475246
0.9503	High Similarity	NPC278329
0.9503	High Similarity	NPC146837
0.9503	High Similarity	NPC101116
0.9503	High Similarity	NPC212099
0.9503	High Similarity	NPC216752
0.9464	High Similarity	NPC197357
0.9464	High Similarity	NPC85316
0.9458	High Similarity	NPC3718
0.9458	High Similarity	NPC186800
0.9458	High Similarity	NPC470667
0.9455	High Similarity	NPC111536
0.9455	High Similarity	NPC271385
0.9455	High Similarity	NPC76128
0.9455	High Similarity	NPC5029
0.9455	High Similarity	NPC30432
0.9401	High Similarity	NPC46958
0.9387	High Similarity	NPC178281
0.9357	High Similarity	NPC105591
0.9353	High Similarity	NPC224557
0.9353	High Similarity	NPC292706
0.9349	High Similarity	NPC477860
0.9349	High Similarity	NPC475161
0.9341	High Similarity	NPC68381
0.9333	High Similarity	NPC222455
0.9286	High Similarity	NPC475233
0.9281	High Similarity	NPC199357
0.9273	High Similarity	NPC63470
0.9268	High Similarity	NPC478022
0.9268	High Similarity	NPC478020
0.9217	High Similarity	NPC259905
0.9212	High Similarity	NPC178851
0.9191	High Similarity	NPC205721
0.9176	High Similarity	NPC212290
0.9167	High Similarity	NPC213052
0.9167	High Similarity	NPC98776
0.9162	High Similarity	NPC298778
0.9146	High Similarity	NPC187934
0.9146	High Similarity	NPC97637
0.9123	High Similarity	NPC315221
0.9112	High Similarity	NPC146803
0.9102	High Similarity	NPC246274
0.9075	High Similarity	NPC241847
0.907	High Similarity	NPC475662
0.907	High Similarity	NPC473717
0.907	High Similarity	NPC473631
0.907	High Similarity	NPC293227
0.907	High Similarity	NPC313452
0.9059	High Similarity	NPC92403
0.9059	High Similarity	NPC170018
0.9059	High Similarity	NPC76112
0.9059	High Similarity	NPC66820
0.9053	High Similarity	NPC472054
0.9048	High Similarity	NPC478021
0.9	High Similarity	NPC474345
0.9	High Similarity	NPC199533
0.9	High Similarity	NPC470454
0.9	High Similarity	NPC307754
0.9	High Similarity	NPC63105
0.9	High Similarity	NPC223735
0.8994	High Similarity	NPC315619
0.8994	High Similarity	NPC294501
0.8977	High Similarity	NPC264302
0.897	High Similarity	NPC73148
0.8966	High Similarity	NPC473686
0.8966	High Similarity	NPC475352
0.8966	High Similarity	NPC221140
0.8966	High Similarity	NPC229817
0.8966	High Similarity	NPC475220
0.8963	High Similarity	NPC53139
0.8953	High Similarity	NPC84494
0.8953	High Similarity	NPC245059
0.892	High Similarity	NPC314672
0.8908	High Similarity	NPC231254
0.8902	High Similarity	NPC470452
0.8902	High Similarity	NPC208651
0.8902	High Similarity	NPC470448
0.8902	High Similarity	NPC206641
0.8902	High Similarity	NPC470453
0.8902	High Similarity	NPC164047
0.8895	High Similarity	NPC47191
0.8876	High Similarity	NPC473202
0.8862	High Similarity	NPC17432
0.8851	High Similarity	NPC478001
0.8848	High Similarity	NPC324736
0.8841	High Similarity	NPC283480
0.8841	High Similarity	NPC148323
0.8837	High Similarity	NPC314489
0.8837	High Similarity	NPC198893
0.8837	High Similarity	NPC232818
0.883	High Similarity	NPC168789
0.8824	High Similarity	NPC313304
0.8824	High Similarity	NPC52598
0.8824	High Similarity	NPC76047
0.8817	High Similarity	NPC324522
0.8817	High Similarity	NPC472058
0.8817	High Similarity	NPC103633
0.8817	High Similarity	NPC470341
0.8817	High Similarity	NPC105414
0.8817	High Similarity	NPC234497
0.881	High Similarity	NPC99216
0.8807	High Similarity	NPC65489
0.8802	High Similarity	NPC44947
0.8795	High Similarity	NPC472320
0.8795	High Similarity	NPC328093
0.8788	High Similarity	NPC23817
0.8788	High Similarity	NPC177742
0.878	High Similarity	NPC192219
0.878	High Similarity	NPC82190
0.878	High Similarity	NPC3449
0.878	High Similarity	NPC174599
0.8772	High Similarity	NPC183441
0.8772	High Similarity	NPC478002
0.8765	High Similarity	NPC470206
0.8765	High Similarity	NPC470207
0.8765	High Similarity	NPC175477
0.8757	High Similarity	NPC477835
0.8757	High Similarity	NPC178173
0.8757	High Similarity	NPC473618
0.875	High Similarity	NPC257566
0.875	High Similarity	NPC124155
0.8743	High Similarity	NPC132111
0.8743	High Similarity	NPC47923
0.8743	High Similarity	NPC18380
0.8743	High Similarity	NPC476203
0.8743	High Similarity	NPC472261
0.8743	High Similarity	NPC303913
0.8735	High Similarity	NPC73511
0.8727	High Similarity	NPC208152
0.8727	High Similarity	NPC78492
0.8721	High Similarity	NPC470335
0.8721	High Similarity	NPC470336
0.8721	High Similarity	NPC154986
0.872	High Similarity	NPC474621
0.872	High Similarity	NPC205172
0.872	High Similarity	NPC474622
0.872	High Similarity	NPC209393
0.8715	High Similarity	NPC470199
0.8715	High Similarity	NPC314459
0.8713	High Similarity	NPC150767
0.8713	High Similarity	NPC78734
0.8701	High Similarity	NPC179947
0.8698	High Similarity	NPC11608
0.8698	High Similarity	NPC469664
0.8698	High Similarity	NPC297404
0.869	High Similarity	NPC472876
0.869	High Similarity	NPC190450
0.869	High Similarity	NPC131745
0.869	High Similarity	NPC15374
0.869	High Similarity	NPC259834
0.8686	High Similarity	NPC208797
0.8686	High Similarity	NPC53680
0.8683	High Similarity	NPC184326
0.8683	High Similarity	NPC271479
0.8683	High Similarity	NPC292863
0.8678	High Similarity	NPC470334
0.8678	High Similarity	NPC472387
0.8678	High Similarity	NPC267549
0.8678	High Similarity	NPC478000
0.8675	High Similarity	NPC161749
0.8675	High Similarity	NPC258035
0.8675	High Similarity	NPC197896
0.8675	High Similarity	NPC156457
0.8675	High Similarity	NPC313163
0.8667	High Similarity	NPC99233
0.8667	High Similarity	NPC226656
0.8667	High Similarity	NPC66508
0.8667	High Similarity	NPC315351
0.8667	High Similarity	NPC316412
0.8663	High Similarity	NPC4200
0.8663	High Similarity	NPC67134
0.8663	High Similarity	NPC47140
0.8663	High Similarity	NPC260263
0.8663	High Similarity	NPC477836
0.8663	High Similarity	NPC256760
0.8659	High Similarity	NPC474534
0.8659	High Similarity	NPC474533
0.8655	High Similarity	NPC229687
0.8655	High Similarity	NPC191653
0.8655	High Similarity	NPC300307
0.8655	High Similarity	NPC53252
0.8647	High Similarity	NPC70441
0.8644	High Similarity	NPC111490
0.8644	High Similarity	NPC261623
0.8639	High Similarity	NPC183672
0.8639	High Similarity	NPC66087
0.8639	High Similarity	NPC179198
0.8639	High Similarity	NPC290160
0.8639	High Similarity	NPC278419
0.8636	High Similarity	NPC321916
0.8631	High Similarity	NPC477629

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 NPC85368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	899
0.2-0.3	1685
0.3-0.4	2658
0.4-0.5	1995
0.5-0.6	1010
0.6-0.7	344
0.7-0.8	128
0.8-0.85	49
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9059	High Similarity	NPD8312	Approved
0.9059	High Similarity	NPD8313	Approved
0.8914	High Similarity	NPD7879	Clinical (unspecified phase)
0.8743	High Similarity	NPD6959	Discontinued
0.8721	High Similarity	NPD6559	Discontinued
0.8675	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD6780	Approved
0.8571	High Similarity	NPD6777	Approved
0.8571	High Similarity	NPD6781	Approved
0.8571	High Similarity	NPD6776	Approved
0.8571	High Similarity	NPD6782	Approved
0.8571	High Similarity	NPD6778	Approved
0.8571	High Similarity	NPD6779	Approved
0.8547	High Similarity	NPD7804	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7074	Phase 3
0.8439	Intermediate Similarity	NPD7054	Approved
0.8432	Intermediate Similarity	NPD7435	Discontinued
0.8404	Intermediate Similarity	NPD8151	Discontinued
0.8391	Intermediate Similarity	NPD7472	Approved
0.8387	Intermediate Similarity	NPD7871	Phase 2
0.8387	Intermediate Similarity	NPD7870	Phase 2
0.8382	Intermediate Similarity	NPD3818	Discontinued
0.838	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD7697	Approved
0.8333	Intermediate Similarity	NPD7696	Phase 3
0.8333	Intermediate Similarity	NPD7698	Approved
0.8324	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD4380	Phase 2
0.8297	Intermediate Similarity	NPD6534	Approved
0.8297	Intermediate Similarity	NPD6535	Approved
0.8295	Intermediate Similarity	NPD7251	Discontinued
0.8276	Intermediate Similarity	NPD3751	Discontinued
0.8266	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6166	Phase 2
0.8254	Intermediate Similarity	NPD7701	Phase 2
0.8253	Intermediate Similarity	NPD3226	Approved
0.8249	Intermediate Similarity	NPD7808	Phase 3
0.8242	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6212	Phase 3
0.8242	Intermediate Similarity	NPD6213	Phase 3
0.822	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD7783	Phase 2
0.8182	Intermediate Similarity	NPD6823	Phase 2
0.8168	Intermediate Similarity	NPD7874	Approved
0.8168	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7819	Suspended
0.8162	Intermediate Similarity	NPD7699	Phase 2
0.8162	Intermediate Similarity	NPD7700	Phase 2
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD3787	Discontinued
0.8146	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7075	Discontinued
0.8125	Intermediate Similarity	NPD7801	Approved
0.8118	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD8455	Phase 2
0.8047	Intermediate Similarity	NPD7411	Suspended
0.8036	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8319	Approved
0.8	Intermediate Similarity	NPD8320	Phase 1
0.8	Intermediate Similarity	NPD1934	Approved
0.7967	Intermediate Similarity	NPD8150	Discontinued
0.7953	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2346	Discontinued
0.7907	Intermediate Similarity	NPD5402	Approved
0.7904	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6801	Discontinued
0.7861	Intermediate Similarity	NPD7768	Phase 2
0.785	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7390	Discontinued
0.7829	Intermediate Similarity	NPD5494	Approved
0.7824	Intermediate Similarity	NPD7458	Discontinued
0.7816	Intermediate Similarity	NPD3749	Approved
0.7798	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7228	Approved
0.7758	Intermediate Similarity	NPD1549	Phase 2
0.7746	Intermediate Similarity	NPD2801	Approved
0.7706	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.768	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6599	Discontinued
0.7665	Intermediate Similarity	NPD4628	Phase 3
0.7657	Intermediate Similarity	NPD3882	Suspended
0.7644	Intermediate Similarity	NPD1465	Phase 2
0.7605	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3817	Phase 2
0.7588	Intermediate Similarity	NPD5401	Approved
0.7586	Intermediate Similarity	NPD37	Approved
0.7584	Intermediate Similarity	NPD7199	Phase 2
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD8059	Phase 3
0.7571	Intermediate Similarity	NPD6234	Discontinued
0.7569	Intermediate Similarity	NPD7177	Discontinued
0.756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4967	Phase 2
0.7557	Intermediate Similarity	NPD4965	Approved
0.7557	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD2796	Approved
0.753	Intermediate Similarity	NPD5406	Approved
0.753	Intermediate Similarity	NPD5408	Approved
0.753	Intermediate Similarity	NPD5405	Approved
0.753	Intermediate Similarity	NPD5404	Approved
0.7529	Intermediate Similarity	NPD6799	Approved
0.7529	Intermediate Similarity	NPD1511	Approved
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1510	Phase 2
0.7462	Intermediate Similarity	NPD7584	Approved
0.7461	Intermediate Similarity	NPD8285	Discontinued
0.7456	Intermediate Similarity	NPD3750	Approved
0.7456	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD1607	Approved
0.7442	Intermediate Similarity	NPD1512	Approved
0.7425	Intermediate Similarity	NPD2935	Discontinued
0.7425	Intermediate Similarity	NPD1551	Phase 2
0.7405	Intermediate Similarity	NPD7240	Approved
0.7405	Intermediate Similarity	NPD7685	Pre-registration
0.7403	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6674	Discontinued
0.7394	Intermediate Similarity	NPD8434	Phase 2
0.7381	Intermediate Similarity	NPD2344	Approved
0.7337	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1240	Approved
0.7329	Intermediate Similarity	NPD1470	Approved
0.7321	Intermediate Similarity	NPD6100	Approved
0.7321	Intermediate Similarity	NPD6099	Approved
0.7317	Intermediate Similarity	NPD2313	Discontinued
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7258	Intermediate Similarity	NPD5953	Discontinued
0.7256	Intermediate Similarity	NPD4625	Phase 3
0.7253	Intermediate Similarity	NPD5711	Approved
0.7253	Intermediate Similarity	NPD5710	Approved
0.7251	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6273	Approved
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2309	Approved
0.7206	Intermediate Similarity	NPD7930	Approved
0.72	Intermediate Similarity	NPD920	Approved
0.7193	Intermediate Similarity	NPD2800	Approved
0.7186	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD2798	Approved
0.7176	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3748	Approved
0.7159	Intermediate Similarity	NPD1653	Approved
0.7158	Intermediate Similarity	NPD7229	Phase 3
0.7157	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1247	Approved
0.7101	Intermediate Similarity	NPD7097	Phase 1
0.7097	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6844	Discontinued
0.7093	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6832	Phase 2
0.7088	Intermediate Similarity	NPD919	Approved
0.7086	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1201	Approved
0.7081	Intermediate Similarity	NPD1091	Approved
0.7079	Intermediate Similarity	NPD7585	Approved
0.7076	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD5761	Phase 2
0.7056	Intermediate Similarity	NPD5760	Phase 2
0.705	Intermediate Similarity	NPD7680	Approved
0.703	Intermediate Similarity	NPD7583	Approved
0.702	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1203	Approved
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1243	Approved
0.699	Remote Similarity	NPD4360	Phase 2
0.699	Remote Similarity	NPD4363	Phase 3
0.6988	Remote Similarity	NPD4908	Phase 1
0.6982	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7999	Approved
0.6977	Remote Similarity	NPD1471	Phase 3
0.6971	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4308	Phase 3
0.6959	Remote Similarity	NPD4287	Approved
0.6946	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD1613	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