NPASS Compound

Structure

NPC469520 OpenBabel07101718302D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.1294 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 1.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0259 1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -0.7986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1261 -0.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9683 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1476 -0.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7366 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 1 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 2.4686 3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7945 -0.2289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9295 -1.1762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 1.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2363 -0.9717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 18 2 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 23 2 0 0 0 0 13 16 1 0 0 0 0 13 24 2 0 0 0 0 14 19 1 0 0 0 0 14 25 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 6 0 0 0 20 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	340.707
LogP:	2.322
LogD:	1.379
LogS:	-4.761
# Rotatable Bonds:	0
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	4.148
Fsp3:	0.2
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:	-5.49
MDCK Permeability:	5.555136340262834e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.591

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	93.7203369140625%
Volume Distribution (VD):	1.032
Pgp-substrate:	4.126908779144287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.641
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.704
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	2.007
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.926
Rat Oral Acute Toxicity:	0.47
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.857
Carcinogencity:	0.812
Eye Corrosion:	0.003
Eye Irritation:	0.137
Respiratory Toxicity:	0.663

Download Data

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

Natural Product: NPC469520

Natural Product ID:	NPC469520
*Common Name:**	Alterperylenol
IUPAC Name:	(1R,12aS,12bR)-1,4,9,12a-tetrahydroxy-2,12b-dihydro-1H-perylene-3,10-dione
Synonyms:	Alterperylenol
Standard InCHIKey:	MTOHOIPTYJIUCH-VOBQZIQPSA-N
Standard InCHI:	InChI=1S/C20H14O6/c21-10-3-1-8-9-2-4-11(22)17-12(23)5-6-20(26,18(9)17)19-14(25)7-13(24)16(10)15(8)19/h1-6,14,19,21-22,25-26H,7H2/t14-,19+,20-/m1/s1
SMILES:	O=C1C[C@@H](O)[C@H]2c3c1c(O)ccc3c1c3[C@]2(O)C=CC(=O)c3c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081908
PubChem CID:	14213481
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002903] Perylenequinones

*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
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19835393]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	=	30000.0	nM	PMID[560079]

☑ 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 NPC469520 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	370
0.1-0.2	1387
0.2-0.3	2937
0.3-0.4	8058
0.4-0.5	11253
0.5-0.6	4920
0.6-0.7	7739
0.7-0.8	5405
0.8-0.85	491
0.85-0.9	127
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC85310
0.9167	High Similarity	NPC142846
0.9097	High Similarity	NPC472135
0.9028	High Similarity	NPC472134
0.8913	High Similarity	NPC314048
0.8913	High Similarity	NPC52407
0.8865	High Similarity	NPC13715
0.8841	High Similarity	NPC70622
0.8811	High Similarity	NPC106519
0.8811	High Similarity	NPC477275
0.8811	High Similarity	NPC91019
0.8811	High Similarity	NPC204045
0.8811	High Similarity	NPC305845
0.8803	High Similarity	NPC190457
0.8786	High Similarity	NPC283088
0.8759	High Similarity	NPC244691
0.8759	High Similarity	NPC471906
0.875	High Similarity	NPC474961
0.875	High Similarity	NPC135524
0.875	High Similarity	NPC239136
0.875	High Similarity	NPC137649
0.875	High Similarity	NPC19631
0.875	High Similarity	NPC257644
0.8733	High Similarity	NPC474824
0.8733	High Similarity	NPC182921
0.8733	High Similarity	NPC470408
0.8733	High Similarity	NPC218870
0.8716	High Similarity	NPC477221
0.8716	High Similarity	NPC478219
0.8714	High Similarity	NPC50924
0.8707	High Similarity	NPC215593
0.8707	High Similarity	NPC290194
0.8696	High Similarity	NPC199253
0.8696	High Similarity	NPC136588
0.869	High Similarity	NPC471682
0.869	High Similarity	NPC296752
0.8681	High Similarity	NPC246638
0.8662	High Similarity	NPC305060
0.8652	High Similarity	NPC80035
0.8643	High Similarity	NPC225051
0.8639	High Similarity	NPC285122
0.8639	High Similarity	NPC314437
0.8639	High Similarity	NPC143685
0.8633	High Similarity	NPC93015
0.8633	High Similarity	NPC474517
0.8633	High Similarity	NPC244699
0.8633	High Similarity	NPC72669
0.863	High Similarity	NPC218866
0.863	High Similarity	NPC84568
0.863	High Similarity	NPC79627
0.863	High Similarity	NPC48130
0.863	High Similarity	NPC300684
0.8623	High Similarity	NPC99731
0.8618	High Similarity	NPC474861
0.8611	High Similarity	NPC181560
0.8611	High Similarity	NPC169452
0.86	High Similarity	NPC477276
0.8592	High Similarity	NPC315275
0.8592	High Similarity	NPC474813
0.8592	High Similarity	NPC155211
0.8582	High Similarity	NPC202225
0.8582	High Similarity	NPC44437
0.8581	High Similarity	NPC37709
0.8581	High Similarity	NPC119767
0.8571	High Similarity	NPC170055
0.8571	High Similarity	NPC471683
0.8562	High Similarity	NPC313047
0.8562	High Similarity	NPC474203
0.8562	High Similarity	NPC451542
0.8562	High Similarity	NPC295712
0.8561	High Similarity	NPC31799
0.8542	High Similarity	NPC138099
0.8542	High Similarity	NPC242994
0.8533	High Similarity	NPC315520
0.8531	High Similarity	NPC245923
0.8531	High Similarity	NPC53414
0.8531	High Similarity	NPC53206
0.8531	High Similarity	NPC471905
0.8514	High Similarity	NPC147250
0.8514	High Similarity	NPC271944
0.8514	High Similarity	NPC110882
0.8514	High Similarity	NPC85393
0.8503	High Similarity	NPC21599
0.8503	High Similarity	NPC227841
0.8503	High Similarity	NPC193703
0.8503	High Similarity	NPC48762
0.8493	Intermediate Similarity	NPC193555
0.8493	Intermediate Similarity	NPC73061
0.8483	Intermediate Similarity	NPC96421
0.8483	Intermediate Similarity	NPC225243
0.8467	Intermediate Similarity	NPC103540
0.8462	Intermediate Similarity	NPC254847
0.8456	Intermediate Similarity	NPC52161
0.8456	Intermediate Similarity	NPC162751
0.8456	Intermediate Similarity	NPC478018
0.8451	Intermediate Similarity	NPC472262
0.8451	Intermediate Similarity	NPC282780
0.8451	Intermediate Similarity	NPC161964
0.8451	Intermediate Similarity	NPC287604
0.8451	Intermediate Similarity	NPC166480
0.8446	Intermediate Similarity	NPC478019
0.8446	Intermediate Similarity	NPC34482
0.844	Intermediate Similarity	NPC58685
0.844	Intermediate Similarity	NPC246693
0.844	Intermediate Similarity	NPC242358
0.844	Intermediate Similarity	NPC110609
0.8435	Intermediate Similarity	NPC174905
0.8435	Intermediate Similarity	NPC293545
0.8431	Intermediate Similarity	NPC478133
0.8431	Intermediate Similarity	NPC266469
0.8429	Intermediate Similarity	NPC55949
0.8429	Intermediate Similarity	NPC147757
0.8421	Intermediate Similarity	NPC478220
0.8417	Intermediate Similarity	NPC48248
0.8417	Intermediate Similarity	NPC247250
0.8417	Intermediate Similarity	NPC282923
0.8417	Intermediate Similarity	NPC767
0.8417	Intermediate Similarity	NPC96024
0.8414	Intermediate Similarity	NPC143438
0.8411	Intermediate Similarity	NPC205766
0.8411	Intermediate Similarity	NPC477914
0.8406	Intermediate Similarity	NPC3224
0.8403	Intermediate Similarity	NPC44960
0.8403	Intermediate Similarity	NPC474110
0.8403	Intermediate Similarity	NPC53001
0.8403	Intermediate Similarity	NPC62272
0.8403	Intermediate Similarity	NPC147418
0.84	Intermediate Similarity	NPC106524
0.84	Intermediate Similarity	NPC290695
0.8397	Intermediate Similarity	NPC137232
0.8397	Intermediate Similarity	NPC472261
0.8394	Intermediate Similarity	NPC74507
0.8394	Intermediate Similarity	NPC234890
0.8389	Intermediate Similarity	NPC470570
0.8389	Intermediate Similarity	NPC136878
0.8387	Intermediate Similarity	NPC324736
0.838	Intermediate Similarity	NPC139074
0.838	Intermediate Similarity	NPC115458
0.838	Intermediate Similarity	NPC213485
0.838	Intermediate Similarity	NPC40524
0.838	Intermediate Similarity	NPC53896
0.838	Intermediate Similarity	NPC267205
0.8378	Intermediate Similarity	NPC10764
0.8377	Intermediate Similarity	NPC478223
0.8369	Intermediate Similarity	NPC41847
0.8369	Intermediate Similarity	NPC205992
0.8369	Intermediate Similarity	NPC471851
0.8366	Intermediate Similarity	NPC478218
0.8366	Intermediate Similarity	NPC474621
0.8366	Intermediate Similarity	NPC474622
0.8365	Intermediate Similarity	NPC472058
0.8365	Intermediate Similarity	NPC324522
0.8365	Intermediate Similarity	NPC470341
0.8365	Intermediate Similarity	NPC105414
0.8365	Intermediate Similarity	NPC234497
0.8357	Intermediate Similarity	NPC146647
0.8357	Intermediate Similarity	NPC34414
0.8345	Intermediate Similarity	NPC61398
0.8345	Intermediate Similarity	NPC4214
0.8345	Intermediate Similarity	NPC87723
0.8345	Intermediate Similarity	NPC173980
0.8345	Intermediate Similarity	NPC416
0.8344	Intermediate Similarity	NPC315772
0.8333	Intermediate Similarity	NPC472618
0.8333	Intermediate Similarity	NPC272268
0.8333	Intermediate Similarity	NPC292863
0.8333	Intermediate Similarity	NPC191976
0.8333	Intermediate Similarity	NPC284495
0.8333	Intermediate Similarity	NPC184326
0.8322	Intermediate Similarity	NPC12070
0.8322	Intermediate Similarity	NPC288089
0.8322	Intermediate Similarity	NPC478160
0.8322	Intermediate Similarity	NPC12402
0.8321	Intermediate Similarity	NPC375356
0.8312	Intermediate Similarity	NPC66029
0.831	Intermediate Similarity	NPC478190
0.831	Intermediate Similarity	NPC17843
0.831	Intermediate Similarity	NPC175738
0.8301	Intermediate Similarity	NPC470340
0.8301	Intermediate Similarity	NPC474533
0.8301	Intermediate Similarity	NPC474534
0.8299	Intermediate Similarity	NPC110810
0.8299	Intermediate Similarity	NPC290550
0.8298	Intermediate Similarity	NPC108129
0.8291	Intermediate Similarity	NPC290160
0.8289	Intermediate Similarity	NPC255641
0.8289	Intermediate Similarity	NPC147735
0.8289	Intermediate Similarity	NPC290954
0.8288	Intermediate Similarity	NPC26924
0.8288	Intermediate Similarity	NPC103337
0.8288	Intermediate Similarity	NPC114620
0.828	Intermediate Similarity	NPC18380
0.8278	Intermediate Similarity	NPC94781
0.8276	Intermediate Similarity	NPC475957
0.8273	Intermediate Similarity	NPC96915
0.8273	Intermediate Similarity	NPC71610
0.8269	Intermediate Similarity	NPC195167
0.8267	Intermediate Similarity	NPC300540
0.8264	Intermediate Similarity	NPC283590
0.8264	Intermediate Similarity	NPC70859

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 NPC469520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	900
0.2-0.3	1538
0.3-0.4	2696
0.4-0.5	2111
0.5-0.6	1073
0.6-0.7	395
0.7-0.8	100
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8503	High Similarity	NPD7390	Discontinued
0.8467	Intermediate Similarity	NPD1470	Approved
0.8462	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD5405	Approved
0.8403	Intermediate Similarity	NPD5408	Approved
0.8403	Intermediate Similarity	NPD5404	Approved
0.8403	Intermediate Similarity	NPD5406	Approved
0.8309	Intermediate Similarity	NPD1201	Approved
0.82	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6959	Discontinued
0.7808	Intermediate Similarity	NPD943	Approved
0.7737	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3300	Phase 2
0.7707	Intermediate Similarity	NPD4380	Phase 2
0.7706	Intermediate Similarity	NPD8150	Discontinued
0.7636	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1510	Phase 2
0.7569	Intermediate Similarity	NPD1164	Approved
0.7561	Intermediate Similarity	NPD6232	Discontinued
0.7532	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7819	Suspended
0.7451	Intermediate Similarity	NPD1549	Phase 2
0.7434	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD3764	Approved
0.7423	Intermediate Similarity	NPD3749	Approved
0.7421	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1607	Approved
0.7345	Intermediate Similarity	NPD6534	Approved
0.7345	Intermediate Similarity	NPD6535	Approved
0.7337	Intermediate Similarity	NPD5844	Phase 1
0.7333	Intermediate Similarity	NPD1240	Approved
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.7284	Intermediate Similarity	NPD1934	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7278	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD2533	Approved
0.7278	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD3019	Approved
0.7273	Intermediate Similarity	NPD2932	Approved
0.7262	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6166	Phase 2
0.7256	Intermediate Similarity	NPD7768	Phase 2
0.7244	Intermediate Similarity	NPD8166	Discontinued
0.7244	Intermediate Similarity	NPD3750	Approved
0.7238	Intermediate Similarity	NPD6780	Approved
0.7238	Intermediate Similarity	NPD6777	Approved
0.7238	Intermediate Similarity	NPD6782	Approved
0.7238	Intermediate Similarity	NPD6781	Approved
0.7238	Intermediate Similarity	NPD6776	Approved
0.7238	Intermediate Similarity	NPD6778	Approved
0.7238	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD5494	Approved
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD7700	Phase 2
0.7222	Intermediate Similarity	NPD7699	Phase 2
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8319	Approved
0.7174	Intermediate Similarity	NPD8320	Phase 1
0.7168	Intermediate Similarity	NPD4955	Approved
0.7168	Intermediate Similarity	NPD5034	Approved
0.7168	Intermediate Similarity	NPD36	Approved
0.7168	Intermediate Similarity	NPD5026	Approved
0.7168	Intermediate Similarity	NPD5028	Approved
0.7168	Intermediate Similarity	NPD4954	Approved
0.7161	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7125	Intermediate Similarity	NPD6273	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.711	Intermediate Similarity	NPD5030	Phase 2
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7107	Intermediate Similarity	NPD1511	Approved
0.7102	Intermediate Similarity	NPD5038	Approved
0.7102	Intermediate Similarity	NPD5037	Approved
0.7097	Intermediate Similarity	NPD2796	Approved
0.7095	Intermediate Similarity	NPD6213	Phase 3
0.7095	Intermediate Similarity	NPD6212	Phase 3
0.7095	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6190	Approved
0.7086	Intermediate Similarity	NPD2313	Discontinued
0.7083	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7871	Phase 2
0.7081	Intermediate Similarity	NPD7870	Phase 2
0.7076	Intermediate Similarity	NPD3818	Discontinued
0.7073	Intermediate Similarity	NPD6801	Discontinued
0.707	Intermediate Similarity	NPD2800	Approved
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5036	Approved
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2801	Approved
0.7025	Intermediate Similarity	NPD3400	Discontinued
0.7019	Intermediate Similarity	NPD1512	Approved
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.6994	Remote Similarity	NPD7074	Phase 3
0.6981	Remote Similarity	NPD2309	Approved
0.698	Remote Similarity	NPD3094	Phase 2
0.6973	Remote Similarity	NPD6823	Phase 2
0.6968	Remote Similarity	NPD7701	Phase 2
0.6957	Remote Similarity	NPD2342	Discontinued
0.6954	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7801	Approved
0.6946	Remote Similarity	NPD3882	Suspended
0.6937	Remote Similarity	NPD7236	Approved
0.6936	Remote Similarity	NPD7054	Approved
0.6933	Remote Similarity	NPD2798	Approved
0.6932	Remote Similarity	NPD5035	Approved
0.6931	Remote Similarity	NPD8151	Discontinued
0.6928	Remote Similarity	NPD1465	Phase 2
0.6928	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD3748	Approved
0.6918	Remote Similarity	NPD4628	Phase 3
0.6913	Remote Similarity	NPD1283	Approved
0.6903	Remote Similarity	NPD6651	Approved
0.6901	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7472	Approved
0.6897	Remote Similarity	NPD3091	Approved
0.6895	Remote Similarity	NPD7874	Approved
0.6895	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4878	Approved
0.6887	Remote Similarity	NPD5736	Approved
0.6886	Remote Similarity	NPD5402	Approved
0.6886	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7177	Discontinued
0.6871	Remote Similarity	NPD3026	Approved
0.6871	Remote Similarity	NPD920	Approved
0.6871	Remote Similarity	NPD3023	Approved
0.6862	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6797	Phase 2
0.6854	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3025	Approved
0.6849	Remote Similarity	NPD3024	Approved
0.6835	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7635	Approved
0.6826	Remote Similarity	NPD5760	Phase 2
0.6826	Remote Similarity	NPD5761	Phase 2
0.6824	Remote Similarity	NPD3092	Approved
0.6824	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5039	Approved
0.6818	Remote Similarity	NPD5031	Approved
0.6818	Remote Similarity	NPD5027	Approved
0.6818	Remote Similarity	NPD7251	Discontinued
0.6818	Remote Similarity	NPD5029	Approved
0.6816	Remote Similarity	NPD8434	Phase 2
0.6813	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4956	Approved
0.6797	Remote Similarity	NPD7008	Discontinued
0.6786	Remote Similarity	NPD74	Approved
0.6786	Remote Similarity	NPD9266	Approved
0.6781	Remote Similarity	NPD9545	Approved
0.678	Remote Similarity	NPD7808	Phase 3
0.678	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD9269	Phase 2
0.6772	Remote Similarity	NPD1551	Phase 2
0.6771	Remote Similarity	NPD7783	Phase 2
0.6771	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD37	Approved
0.6759	Remote Similarity	NPD9493	Approved
0.6748	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6599	Discontinued
0.6744	Remote Similarity	NPD5710	Approved
0.6744	Remote Similarity	NPD5711	Approved
0.6743	Remote Similarity	NPD6020	Phase 2
0.6739	Remote Similarity	NPD1237	Approved
0.6736	Remote Similarity	NPD5951	Approved
0.6735	Remote Similarity	NPD9268	Approved
0.6735	Remote Similarity	NPD1651	Approved
0.6731	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1471	Phase 3
0.6727	Remote Similarity	NPD7239	Suspended
0.6726	Remote Similarity	NPD8455	Phase 2
0.6714	Remote Similarity	NPD9267	Approved
0.6714	Remote Similarity	NPD9264	Approved
0.6714	Remote Similarity	NPD9263	Approved
0.6711	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1281	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