NPASS Compound

Structure

NPC470407 OpenBabel07101718242D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.0123 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2711 -0.0517 0.0000 C 0 0 0 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 3.4641 -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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5640 -0.7588 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 1.7321 -0.0000 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 -1.7321 0.0000 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 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 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 3.4641 -2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 -2.4676 0.4914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 8 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 19 2 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 21 24 2 0 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.15
Volume:	368.912
LogP:	4.993
LogD:	3.344
LogS:	-4.371
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	3.601
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	1.7645985280978493e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.119
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.409

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.95951080322266%
Volume Distribution (VD):	0.45
Pgp-substrate:	3.249253749847412%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.624
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	13.649
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.467
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.735
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.954
Carcinogencity:	0.686
Eye Corrosion:	0.003
Eye Irritation:	0.377
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC470407

Natural Product ID:	NPC470407
*Common Name:**	7,8,9,10-Tetrahydro-9-Hydroxy-4-Methoxy-9-Propyltetracene-6,11-Dione
IUPAC Name:	(3R)-3-hydroxy-10-methoxy-3-propyl-2,4-dihydro-1H-tetracene-5,12-dione
Synonyms:
Standard InCHIKey:	PFGHUSSKUIXHKF-JOCHJYFZSA-N
Standard InCHI:	InChI=1S/C22H22O4/c1-3-8-22(25)9-7-14-18(12-22)21(24)16-10-13-5-4-6-19(26-2)15(13)11-17(16)20(14)23/h4-6,10-11,25H,3,7-9,12H2,1-2H3/t22-/m1/s1
SMILES:	CCCC1(CCC2=C(C1)C(=O)C3=C(C2=O)C=C4C(=C3)C=CC=C4OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2024357
PubChem CID:	70696180
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	>	70000.0	nM	PMID[510241]

☑ 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 NPC470407 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	349
0.1-0.2	1591
0.2-0.3	3417
0.3-0.4	9213
0.4-0.5	9578
0.5-0.6	4156
0.6-0.7	8449
0.7-0.8	5547
0.8-0.85	345
0.85-0.9	46
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9281	High Similarity	NPC53016
0.9179	High Similarity	NPC183103
0.9118	High Similarity	NPC22644
0.9111	High Similarity	NPC470406
0.9071	High Similarity	NPC69755
0.8986	High Similarity	NPC186647
0.8913	High Similarity	NPC471670
0.8904	High Similarity	NPC144283
0.8889	High Similarity	NPC478018
0.8881	High Similarity	NPC478019
0.8828	High Similarity	NPC472841
0.8824	High Similarity	NPC239134
0.8786	High Similarity	NPC475104
0.8768	High Similarity	NPC50924
0.8767	High Similarity	NPC80370
0.8731	High Similarity	NPC474737
0.8731	High Similarity	NPC177925
0.8723	High Similarity	NPC1268
0.8686	High Similarity	NPC164295
0.8681	High Similarity	NPC472836
0.8676	High Similarity	NPC57552
0.8671	High Similarity	NPC201297
0.8667	High Similarity	NPC428300
0.8649	High Similarity	NPC306011
0.8649	High Similarity	NPC472838
0.8649	High Similarity	NPC230848
0.8633	High Similarity	NPC1249
0.863	High Similarity	NPC58373
0.863	High Similarity	NPC478163
0.8623	High Similarity	NPC312560
0.8603	High Similarity	NPC96024
0.8601	High Similarity	NPC124365
0.86	High Similarity	NPC226656
0.86	High Similarity	NPC66508
0.8582	High Similarity	NPC301341
0.8582	High Similarity	NPC290601
0.8581	High Similarity	NPC58310
0.8581	High Similarity	NPC295977
0.8571	High Similarity	NPC474107
0.8571	High Similarity	NPC22222
0.8571	High Similarity	NPC281513
0.8552	High Similarity	NPC471451
0.8551	High Similarity	NPC244699
0.8551	High Similarity	NPC205360
0.8543	High Similarity	NPC276231
0.854	High Similarity	NPC146647
0.854	High Similarity	NPC34414
0.8514	High Similarity	NPC329933
0.8511	High Similarity	NPC475549
0.8511	High Similarity	NPC141934
0.8503	High Similarity	NPC56433
0.8503	High Similarity	NPC118027
0.8503	High Similarity	NPC245584
0.8503	High Similarity	NPC126767
0.8503	High Similarity	NPC190648
0.8503	High Similarity	NPC289042
0.8503	High Similarity	NPC34802
0.8503	High Similarity	NPC312929
0.85	High Similarity	NPC274876
0.8493	Intermediate Similarity	NPC49282
0.8483	Intermediate Similarity	NPC167663
0.8478	Intermediate Similarity	NPC245395
0.8478	Intermediate Similarity	NPC27659
0.8478	Intermediate Similarity	NPC55949
0.8478	Intermediate Similarity	NPC470725
0.8477	Intermediate Similarity	NPC478161
0.8477	Intermediate Similarity	NPC3898
0.8477	Intermediate Similarity	NPC478159
0.8467	Intermediate Similarity	NPC164912
0.8462	Intermediate Similarity	NPC477408
0.8462	Intermediate Similarity	NPC223336
0.8456	Intermediate Similarity	NPC255641
0.8456	Intermediate Similarity	NPC470568
0.8456	Intermediate Similarity	NPC290954
0.8451	Intermediate Similarity	NPC284184
0.844	Intermediate Similarity	NPC88065
0.844	Intermediate Similarity	NPC89504
0.844	Intermediate Similarity	NPC283088
0.844	Intermediate Similarity	NPC95485
0.844	Intermediate Similarity	NPC80035
0.8435	Intermediate Similarity	NPC300540
0.8431	Intermediate Similarity	NPC324736
0.8429	Intermediate Similarity	NPC53896
0.8429	Intermediate Similarity	NPC225051
0.8429	Intermediate Similarity	NPC59459
0.8425	Intermediate Similarity	NPC260152
0.8425	Intermediate Similarity	NPC308006
0.8425	Intermediate Similarity	NPC471305
0.8421	Intermediate Similarity	NPC279605
0.8421	Intermediate Similarity	NPC213401
0.8414	Intermediate Similarity	NPC169214
0.8414	Intermediate Similarity	NPC229218
0.8414	Intermediate Similarity	NPC192597
0.8414	Intermediate Similarity	NPC141817
0.8414	Intermediate Similarity	NPC176030
0.8411	Intermediate Similarity	NPC329844
0.84	Intermediate Similarity	NPC474414
0.84	Intermediate Similarity	NPC470569
0.84	Intermediate Similarity	NPC118427
0.84	Intermediate Similarity	NPC473201
0.84	Intermediate Similarity	NPC302783
0.8377	Intermediate Similarity	NPC284495
0.837	Intermediate Similarity	NPC182646
0.8367	Intermediate Similarity	NPC73416
0.8367	Intermediate Similarity	NPC160777
0.8366	Intermediate Similarity	NPC474637
0.8366	Intermediate Similarity	NPC67197
0.8357	Intermediate Similarity	NPC58685
0.8356	Intermediate Similarity	NPC163948
0.8356	Intermediate Similarity	NPC66593
0.8356	Intermediate Similarity	NPC84266
0.8344	Intermediate Similarity	NPC154683
0.8344	Intermediate Similarity	NPC40356
0.8333	Intermediate Similarity	NPC294646
0.8333	Intermediate Similarity	NPC48248
0.8333	Intermediate Similarity	NPC147735
0.8333	Intermediate Similarity	NPC205766
0.8323	Intermediate Similarity	NPC472261
0.8322	Intermediate Similarity	NPC36868
0.8322	Intermediate Similarity	NPC472839
0.8321	Intermediate Similarity	NPC254492
0.8312	Intermediate Similarity	NPC245891
0.8312	Intermediate Similarity	NPC104876
0.8311	Intermediate Similarity	NPC39361
0.8309	Intermediate Similarity	NPC75432
0.8309	Intermediate Similarity	NPC56332
0.8309	Intermediate Similarity	NPC199273
0.8301	Intermediate Similarity	NPC288353
0.8301	Intermediate Similarity	NPC478223
0.8299	Intermediate Similarity	NPC19896
0.8299	Intermediate Similarity	NPC309169
0.8299	Intermediate Similarity	NPC193703
0.8299	Intermediate Similarity	NPC21599
0.8299	Intermediate Similarity	NPC196941
0.8298	Intermediate Similarity	NPC263817
0.8291	Intermediate Similarity	NPC105414
0.8291	Intermediate Similarity	NPC234497
0.8291	Intermediate Similarity	NPC324522
0.8291	Intermediate Similarity	NPC470341
0.8291	Intermediate Similarity	NPC472058
0.8289	Intermediate Similarity	NPC210942
0.8289	Intermediate Similarity	NPC208806
0.8289	Intermediate Similarity	NPC169990
0.8288	Intermediate Similarity	NPC182255
0.8288	Intermediate Similarity	NPC94076
0.8288	Intermediate Similarity	NPC49108
0.8286	Intermediate Similarity	NPC93015
0.8286	Intermediate Similarity	NPC279596
0.828	Intermediate Similarity	NPC472057
0.828	Intermediate Similarity	NPC472051
0.828	Intermediate Similarity	NPC26386
0.8278	Intermediate Similarity	NPC474417
0.8278	Intermediate Similarity	NPC132990
0.8278	Intermediate Similarity	NPC149526
0.8278	Intermediate Similarity	NPC46882
0.8273	Intermediate Similarity	NPC276238
0.8267	Intermediate Similarity	NPC10027
0.8267	Intermediate Similarity	NPC288036
0.8267	Intermediate Similarity	NPC65589
0.8267	Intermediate Similarity	NPC472837
0.8267	Intermediate Similarity	NPC100985
0.8267	Intermediate Similarity	NPC97029
0.8267	Intermediate Similarity	NPC97028
0.8267	Intermediate Similarity	NPC158338
0.8267	Intermediate Similarity	NPC65775
0.8264	Intermediate Similarity	NPC233707
0.8264	Intermediate Similarity	NPC13715
0.8261	Intermediate Similarity	NPC45537
0.8261	Intermediate Similarity	NPC72667
0.8258	Intermediate Similarity	NPC470342
0.8258	Intermediate Similarity	NPC472052
0.8258	Intermediate Similarity	NPC472060
0.8255	Intermediate Similarity	NPC52692
0.8252	Intermediate Similarity	NPC155211
0.8247	Intermediate Similarity	NPC201127
0.8243	Intermediate Similarity	NPC34482
0.8243	Intermediate Similarity	NPC478160
0.8243	Intermediate Similarity	NPC225351
0.8239	Intermediate Similarity	NPC202225
0.8231	Intermediate Similarity	NPC3732
0.8231	Intermediate Similarity	NPC50954
0.8231	Intermediate Similarity	NPC472840
0.8227	Intermediate Similarity	NPC474340
0.8224	Intermediate Similarity	NPC27615
0.8219	Intermediate Similarity	NPC149780
0.8219	Intermediate Similarity	NPC84273
0.8214	Intermediate Similarity	NPC253488
0.8214	Intermediate Similarity	NPC108129
0.82	Intermediate Similarity	NPC7025
0.82	Intermediate Similarity	NPC2569
0.82	Intermediate Similarity	NPC256672
0.82	Intermediate Similarity	NPC474556
0.82	Intermediate Similarity	NPC172329
0.82	Intermediate Similarity	NPC472056
0.82	Intermediate Similarity	NPC27221
0.8194	Intermediate Similarity	NPC470721
0.8194	Intermediate Similarity	NPC156888
0.8194	Intermediate Similarity	NPC264022
0.8194	Intermediate Similarity	NPC24394
0.8194	Intermediate Similarity	NPC470722

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 NPC470407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	984
0.2-0.3	1244
0.3-0.4	2421
0.4-0.5	2240
0.5-0.6	1234
0.6-0.7	558
0.7-0.8	145
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8392	Intermediate Similarity	NPD2346	Discontinued
0.8345	Intermediate Similarity	NPD7003	Approved
0.8271	Intermediate Similarity	NPD1651	Approved
0.8175	Intermediate Similarity	NPD1283	Approved
0.8162	Intermediate Similarity	NPD3972	Approved
0.8146	Intermediate Similarity	NPD3226	Approved
0.8026	Intermediate Similarity	NPD7458	Discontinued
0.8026	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2799	Discontinued
0.7956	Intermediate Similarity	NPD1281	Approved
0.7945	Intermediate Similarity	NPD2935	Discontinued
0.7935	Intermediate Similarity	NPD7819	Suspended
0.7929	Intermediate Similarity	NPD2798	Approved
0.7925	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD1876	Approved
0.7905	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2344	Approved
0.7888	Intermediate Similarity	NPD7473	Discontinued
0.7877	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1470	Approved
0.7832	Intermediate Similarity	NPD2313	Discontinued
0.781	Intermediate Similarity	NPD4626	Approved
0.777	Intermediate Similarity	NPD1471	Phase 3
0.777	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6959	Discontinued
0.774	Intermediate Similarity	NPD1607	Approved
0.7733	Intermediate Similarity	NPD3750	Approved
0.7724	Intermediate Similarity	NPD2979	Phase 3
0.7712	Intermediate Similarity	NPD6273	Approved
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7682	Intermediate Similarity	NPD2309	Approved
0.7647	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3748	Approved
0.7635	Intermediate Similarity	NPD4308	Phase 3
0.7635	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD7177	Discontinued
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.7609	Intermediate Similarity	NPD5691	Approved
0.7603	Intermediate Similarity	NPD1240	Approved
0.7584	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD5405	Approved
0.7584	Intermediate Similarity	NPD5408	Approved
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.7571	Intermediate Similarity	NPD1201	Approved
0.7554	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.7518	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7468	Intermediate Similarity	NPD7411	Suspended
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD2531	Phase 2
0.7467	Intermediate Similarity	NPD2796	Approved
0.7467	Intermediate Similarity	NPD2438	Suspended
0.7467	Intermediate Similarity	NPD6100	Approved
0.7466	Intermediate Similarity	NPD3764	Approved
0.7466	Intermediate Similarity	NPD3268	Approved
0.7465	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3749	Approved
0.7447	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7028	Phase 2
0.7397	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD1608	Approved
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5494	Approved
0.7361	Intermediate Similarity	NPD2797	Approved
0.7351	Intermediate Similarity	NPD4476	Approved
0.7351	Intermediate Similarity	NPD4477	Approved
0.7329	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1611	Approved
0.7308	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2932	Approved
0.7303	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.729	Intermediate Similarity	NPD3300	Phase 2
0.7289	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7279	Intermediate Similarity	NPD7008	Discontinued
0.7267	Intermediate Similarity	NPD2801	Approved
0.726	Intermediate Similarity	NPD9494	Approved
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7241	Intermediate Similarity	NPD3267	Approved
0.7241	Intermediate Similarity	NPD3266	Approved
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7234	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5536	Phase 2
0.7211	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD1934	Approved
0.7205	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.7183	Intermediate Similarity	NPD3019	Approved
0.7183	Intermediate Similarity	NPD17	Approved
0.7181	Intermediate Similarity	NPD8032	Phase 2
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3882	Suspended
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.7162	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD8166	Discontinued
0.716	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7134	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD2649	Approved
0.7125	Intermediate Similarity	NPD2651	Approved
0.7123	Intermediate Similarity	NPD1203	Approved
0.7122	Intermediate Similarity	NPD5951	Approved
0.7117	Intermediate Similarity	NPD5977	Approved
0.7117	Intermediate Similarity	NPD2296	Approved
0.7117	Intermediate Similarity	NPD5978	Approved
0.7115	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD411	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6279	Approved
0.7099	Intermediate Similarity	NPD6280	Approved
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD7577	Discontinued
0.7097	Intermediate Similarity	NPD2800	Approved
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4624	Approved
0.707	Intermediate Similarity	NPD7236	Approved
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7047	Intermediate Similarity	NPD7095	Approved
0.7044	Intermediate Similarity	NPD1512	Approved
0.7039	Intermediate Similarity	NPD4097	Suspended
0.7039	Intermediate Similarity	NPD6651	Approved
0.7035	Intermediate Similarity	NPD6559	Discontinued
0.7034	Intermediate Similarity	NPD9717	Approved
0.703	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.702	Intermediate Similarity	NPD943	Approved
0.7014	Intermediate Similarity	NPD3026	Approved
0.7014	Intermediate Similarity	NPD3847	Discontinued
0.7014	Intermediate Similarity	NPD3023	Approved
0.7013	Intermediate Similarity	NPD1551	Phase 2
0.7012	Intermediate Similarity	NPD3817	Phase 2
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7007	Intermediate Similarity	NPD1164	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD7427	Discontinued
0.7	Intermediate Similarity	NPD920	Approved
0.6993	Remote Similarity	NPD3025	Approved
0.6993	Remote Similarity	NPD3024	Approved
0.6987	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1243	Approved
0.6986	Remote Similarity	NPD1669	Approved
0.6985	Remote Similarity	NPD2342	Discontinued
0.6982	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7635	Approved
0.6974	Remote Similarity	NPD447	Suspended
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2353	Approved
0.6964	Remote Similarity	NPD5710	Approved
0.6964	Remote Similarity	NPD3787	Discontinued
0.6964	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD7239	Suspended
0.6957	Remote Similarity	NPD4141	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