NPASS Compound

Structure

NPC472135 OpenBabel07101718292D 25 30 0 0 1 0 0 0 0 0999 V2000 3.8576 -2.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5948 -0.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 -1.8759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 0.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -1.9757 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 2.4686 -0.7728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4369 -1.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 -0.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -1.2070 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 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7424 -0.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.8660 -0.5000 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 5.2632 -0.5439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3981 0.4034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 1 4 2 0 0 0 0 1 7 1 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 3 1 1 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 22 2 0 0 0 0 12 17 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 14 1 1 0 0 0 15 19 1 0 0 0 0 17 18 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 18 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.07
Volume:	323.36
LogP:	5.467
LogD:	2.941
LogS:	-5.909
# Rotatable Bonds:	0
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	3.357
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.225
MDCK Permeability:	4.922636890114518e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.801
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	90.96538543701172%
Volume Distribution (VD):	0.421
Pgp-substrate:	12.122091293334961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	3.343
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.514
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.704
Rat Oral Acute Toxicity:	0.44
Maximum Recommended Daily Dose:	0.354
Skin Sensitization:	0.681
Carcinogencity:	0.901
Eye Corrosion:	0.004
Eye Irritation:	0.404
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC472135

Natural Product ID:	NPC472135
*Common Name:**	WJEBWULXGPDPBD-BRPFIRHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WJEBWULXGPDPBD-BRPFIRHGSA-N
Standard InCHI:	InChI=1S/C20H12O5/c21-10-4-1-7-8-2-5-12(23)17-14(8)15(19-20(25-19)18(17)24)9-3-6-11(22)16(10)13(7)9/h1-6,9,15,19-21,23H/t9-,15-,19+,20-/m0/s1
SMILES:	C1=CC(=O)C2=C(C=CC3=C2C1C4C5C(O5)C(=O)C6=C(C=CC3=C46)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338988
PubChem CID:	n.a.
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
NPO33081	alternaria tenuissima que1se	Species	Pleosporaceae	Eukaryota	endophyte of Quercus emoryi	n.a.	n.a.	PMID[25260957]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	33.0	%	PMID[508910]

☑ 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 NPC472135 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	401
0.1-0.2	1481
0.2-0.3	3058
0.3-0.4	8318
0.4-0.5	10868
0.5-0.6	5027
0.6-0.7	7969
0.7-0.8	5282
0.8-0.85	266
0.85-0.9	21
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9648	High Similarity	NPC472134
0.958	High Similarity	NPC215593
0.9514	High Similarity	NPC142846
0.9097	High Similarity	NPC469520
0.8889	High Similarity	NPC114620
0.8889	High Similarity	NPC103337
0.8882	High Similarity	NPC478133
0.8836	High Similarity	NPC85310
0.8836	High Similarity	NPC308572
0.8667	High Similarity	NPC119767
0.8599	High Similarity	NPC478134
0.8591	High Similarity	NPC300684
0.8591	High Similarity	NPC218866
0.8591	High Similarity	NPC48130
0.8591	High Similarity	NPC84568
0.8553	High Similarity	NPC120171
0.8553	High Similarity	NPC478219
0.8533	High Similarity	NPC478160
0.8533	High Similarity	NPC170055
0.8514	High Similarity	NPC110810
0.8497	Intermediate Similarity	NPC477914
0.8491	Intermediate Similarity	NPC290160
0.8483	Intermediate Similarity	NPC283088
0.8477	Intermediate Similarity	NPC147250
0.8472	Intermediate Similarity	NPC52407
0.8472	Intermediate Similarity	NPC314048
0.8467	Intermediate Similarity	NPC471906
0.8467	Intermediate Similarity	NPC477913
0.8462	Intermediate Similarity	NPC72669
0.8462	Intermediate Similarity	NPC474517
0.8456	Intermediate Similarity	NPC19631
0.8456	Intermediate Similarity	NPC239136
0.8435	Intermediate Similarity	NPC13715
0.8418	Intermediate Similarity	NPC184326
0.8418	Intermediate Similarity	NPC292863
0.8414	Intermediate Similarity	NPC50924
0.8403	Intermediate Similarity	NPC70622
0.84	Intermediate Similarity	NPC478164
0.8397	Intermediate Similarity	NPC314257
0.8389	Intermediate Similarity	NPC477275
0.8389	Intermediate Similarity	NPC106519
0.8389	Intermediate Similarity	NPC91019
0.8366	Intermediate Similarity	NPC290695
0.8366	Intermediate Similarity	NPC106524
0.8366	Intermediate Similarity	NPC94781
0.8365	Intermediate Similarity	NPC137232
0.8365	Intermediate Similarity	NPC18380
0.8355	Intermediate Similarity	NPC285122
0.8354	Intermediate Similarity	NPC195167
0.8345	Intermediate Similarity	NPC225051
0.8344	Intermediate Similarity	NPC79627
0.8344	Intermediate Similarity	NPC29932
0.8333	Intermediate Similarity	NPC244699
0.8333	Intermediate Similarity	NPC182921
0.8333	Intermediate Similarity	NPC474824
0.8333	Intermediate Similarity	NPC218870
0.8333	Intermediate Similarity	NPC470408
0.8333	Intermediate Similarity	NPC478218
0.8323	Intermediate Similarity	NPC477276
0.8323	Intermediate Similarity	NPC205918
0.8322	Intermediate Similarity	NPC99731
0.8312	Intermediate Similarity	NPC477221
0.8311	Intermediate Similarity	NPC173980
0.8301	Intermediate Similarity	NPC162751
0.8301	Intermediate Similarity	NPC52161
0.8301	Intermediate Similarity	NPC5568
0.8301	Intermediate Similarity	NPC290194
0.8299	Intermediate Similarity	NPC155211
0.8299	Intermediate Similarity	NPC474813
0.8289	Intermediate Similarity	NPC474630
0.8288	Intermediate Similarity	NPC161964
0.8288	Intermediate Similarity	NPC287604
0.8288	Intermediate Similarity	NPC472262
0.828	Intermediate Similarity	NPC266469
0.8278	Intermediate Similarity	NPC313047
0.8278	Intermediate Similarity	NPC451542
0.8278	Intermediate Similarity	NPC296752
0.8278	Intermediate Similarity	NPC295712
0.8278	Intermediate Similarity	NPC474203
0.8276	Intermediate Similarity	NPC309430
0.8267	Intermediate Similarity	NPC246638
0.8267	Intermediate Similarity	NPC305845
0.8267	Intermediate Similarity	NPC204045
0.8264	Intermediate Similarity	NPC27659
0.8264	Intermediate Similarity	NPC199253
0.8264	Intermediate Similarity	NPC136588
0.8258	Intermediate Similarity	NPC315520
0.8258	Intermediate Similarity	NPC205766
0.8255	Intermediate Similarity	NPC190457
0.8255	Intermediate Similarity	NPC26924
0.8252	Intermediate Similarity	NPC96024
0.825	Intermediate Similarity	NPC472261
0.8243	Intermediate Similarity	NPC245923
0.8243	Intermediate Similarity	NPC305060
0.8235	Intermediate Similarity	NPC470570
0.8235	Intermediate Similarity	NPC136878
0.8231	Intermediate Similarity	NPC80035
0.8228	Intermediate Similarity	NPC474861
0.8228	Intermediate Similarity	NPC478223
0.8224	Intermediate Similarity	NPC48762
0.8224	Intermediate Similarity	NPC244691
0.8224	Intermediate Similarity	NPC227841
0.8224	Intermediate Similarity	NPC193703
0.8224	Intermediate Similarity	NPC21599
0.8219	Intermediate Similarity	NPC78307
0.8219	Intermediate Similarity	NPC171968
0.8217	Intermediate Similarity	NPC472211
0.8212	Intermediate Similarity	NPC257644
0.8212	Intermediate Similarity	NPC474300
0.8212	Intermediate Similarity	NPC135524
0.8212	Intermediate Similarity	NPC137649
0.8212	Intermediate Similarity	NPC474961
0.8207	Intermediate Similarity	NPC41847
0.8205	Intermediate Similarity	NPC230848
0.82	Intermediate Similarity	NPC169452
0.82	Intermediate Similarity	NPC181560
0.82	Intermediate Similarity	NPC96421
0.82	Intermediate Similarity	NPC315578
0.82	Intermediate Similarity	NPC225243
0.8194	Intermediate Similarity	NPC280753
0.8194	Intermediate Similarity	NPC44378
0.8187	Intermediate Similarity	NPC284495
0.8182	Intermediate Similarity	NPC476821
0.8182	Intermediate Similarity	NPC37709
0.8176	Intermediate Similarity	NPC86524
0.8176	Intermediate Similarity	NPC38158
0.817	Intermediate Similarity	NPC34482
0.8169	Intermediate Similarity	NPC103540
0.8165	Intermediate Similarity	NPC66029
0.8163	Intermediate Similarity	NPC44437
0.8158	Intermediate Similarity	NPC471682
0.8158	Intermediate Similarity	NPC476473
0.8158	Intermediate Similarity	NPC100242
0.8158	Intermediate Similarity	NPC354984
0.8158	Intermediate Similarity	NPC174905
0.8158	Intermediate Similarity	NPC293545
0.8153	Intermediate Similarity	NPC474533
0.8153	Intermediate Similarity	NPC474534
0.8153	Intermediate Similarity	NPC478220
0.8151	Intermediate Similarity	NPC58685
0.8138	Intermediate Similarity	NPC198305
0.8138	Intermediate Similarity	NPC55949
0.8137	Intermediate Similarity	NPC219686
0.8133	Intermediate Similarity	NPC138099
0.8133	Intermediate Similarity	NPC242994
0.8125	Intermediate Similarity	NPC237225
0.8125	Intermediate Similarity	NPC48248
0.8125	Intermediate Similarity	NPC165257
0.8125	Intermediate Similarity	NPC324736
0.8125	Intermediate Similarity	NPC282923
0.8125	Intermediate Similarity	NPC471750
0.8125	Intermediate Similarity	NPC228654
0.8121	Intermediate Similarity	NPC261292
0.8121	Intermediate Similarity	NPC44960
0.8121	Intermediate Similarity	NPC301915
0.8121	Intermediate Similarity	NPC53414
0.8121	Intermediate Similarity	NPC53001
0.8121	Intermediate Similarity	NPC474110
0.8121	Intermediate Similarity	NPC62272
0.8121	Intermediate Similarity	NPC475957
0.8121	Intermediate Similarity	NPC471905
0.8121	Intermediate Similarity	NPC53206
0.8117	Intermediate Similarity	NPC271944
0.8117	Intermediate Similarity	NPC143685
0.8117	Intermediate Similarity	NPC51513
0.8117	Intermediate Similarity	NPC314437
0.8117	Intermediate Similarity	NPC202112
0.8117	Intermediate Similarity	NPC110882
0.8117	Intermediate Similarity	NPC85393
0.8112	Intermediate Similarity	NPC231774
0.8112	Intermediate Similarity	NPC3224
0.8108	Intermediate Similarity	NPC283590
0.8108	Intermediate Similarity	NPC130899
0.8108	Intermediate Similarity	NPC61153
0.8108	Intermediate Similarity	NPC70859
0.8101	Intermediate Similarity	NPC209393
0.8101	Intermediate Similarity	NPC205172
0.8099	Intermediate Similarity	NPC173978
0.8099	Intermediate Similarity	NPC164014
0.8095	Intermediate Similarity	NPC53896
0.8095	Intermediate Similarity	NPC115458
0.8095	Intermediate Similarity	NPC267205
0.8095	Intermediate Similarity	NPC254603
0.8092	Intermediate Similarity	NPC73061
0.8092	Intermediate Similarity	NPC69755
0.8092	Intermediate Similarity	NPC201297
0.8092	Intermediate Similarity	NPC193555
0.8086	Intermediate Similarity	NPC478229
0.8086	Intermediate Similarity	NPC187934
0.8086	Intermediate Similarity	NPC15374
0.8086	Intermediate Similarity	NPC97637
0.8086	Intermediate Similarity	NPC315772
0.8082	Intermediate Similarity	NPC93015
0.8082	Intermediate Similarity	NPC205992
0.8082	Intermediate Similarity	NPC471851
0.8079	Intermediate Similarity	NPC42262
0.8079	Intermediate Similarity	NPC168471
0.8079	Intermediate Similarity	NPC37992
0.8079	Intermediate Similarity	NPC220496
0.8079	Intermediate Similarity	NPC241349

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 NPC472135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	927
0.2-0.3	1494
0.3-0.4	2752
0.4-0.5	2074
0.5-0.6	1060
0.6-0.7	403
0.7-0.8	83
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8224	Intermediate Similarity	NPD7390	Discontinued
0.8169	Intermediate Similarity	NPD1470	Approved
0.8143	Intermediate Similarity	NPD1201	Approved
0.8121	Intermediate Similarity	NPD5404	Approved
0.8121	Intermediate Similarity	NPD5405	Approved
0.8121	Intermediate Similarity	NPD5408	Approved
0.8121	Intermediate Similarity	NPD5406	Approved
0.8054	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6959	Discontinued
0.7935	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3300	Phase 2
0.7688	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD4380	Phase 2
0.7625	Intermediate Similarity	NPD3226	Approved
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1510	Phase 2
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7548	Intermediate Similarity	NPD1549	Phase 2
0.7546	Intermediate Similarity	NPD7819	Suspended
0.7546	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6166	Phase 2
0.7456	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7003	Approved
0.744	Intermediate Similarity	NPD6232	Discontinued
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD943	Approved
0.7417	Intermediate Similarity	NPD3764	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7389	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1934	Approved
0.7375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7349	Intermediate Similarity	NPD7768	Phase 2
0.7342	Intermediate Similarity	NPD3750	Approved
0.7342	Intermediate Similarity	NPD8166	Discontinued
0.7338	Intermediate Similarity	NPD1607	Approved
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD6534	Approved
0.7333	Intermediate Similarity	NPD6535	Approved
0.7329	Intermediate Similarity	NPD1512	Approved
0.7326	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5844	Phase 1
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1240	Approved
0.7317	Intermediate Similarity	NPD7411	Suspended
0.7315	Intermediate Similarity	NPD1164	Approved
0.7308	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD3749	Approved
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7258	Intermediate Similarity	NPD8320	Phase 1
0.7258	Intermediate Similarity	NPD8319	Approved
0.7246	Intermediate Similarity	NPD3882	Suspended
0.7244	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD5494	Approved
0.7213	Intermediate Similarity	NPD7700	Phase 2
0.7213	Intermediate Similarity	NPD7699	Phase 2
0.7205	Intermediate Similarity	NPD1511	Approved
0.7204	Intermediate Similarity	NPD7435	Discontinued
0.7202	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2796	Approved
0.7188	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD3019	Approved
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7128	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6273	Approved
0.7112	Intermediate Similarity	NPD7697	Approved
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7112	Intermediate Similarity	NPD7698	Approved
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7099	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD5402	Approved
0.7078	Intermediate Similarity	NPD2313	Discontinued
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.7069	Intermediate Similarity	NPD7177	Discontinued
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1471	Phase 3
0.7041	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7236	Approved
0.7032	Intermediate Similarity	NPD6663	Approved
0.7025	Intermediate Similarity	NPD3748	Approved
0.7024	Intermediate Similarity	NPD2801	Approved
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.6995	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6213	Phase 3
0.6995	Remote Similarity	NPD6212	Phase 3
0.6993	Remote Similarity	NPD5736	Approved
0.6989	Remote Similarity	NPD7074	Phase 3
0.6979	Remote Similarity	NPD7874	Approved
0.6979	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2309	Approved
0.6971	Remote Similarity	NPD3818	Discontinued
0.697	Remote Similarity	NPD5403	Approved
0.6966	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7701	Phase 2
0.6959	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2800	Approved
0.6951	Remote Similarity	NPD5401	Approved
0.6944	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7801	Approved
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7054	Approved
0.6928	Remote Similarity	NPD2798	Approved
0.6908	Remote Similarity	NPD1283	Approved
0.6893	Remote Similarity	NPD7472	Approved
0.6879	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD1247	Approved
0.6875	Remote Similarity	NPD1551	Phase 2
0.6872	Remote Similarity	NPD5034	Approved
0.6872	Remote Similarity	NPD4954	Approved
0.6872	Remote Similarity	NPD36	Approved
0.6872	Remote Similarity	NPD5028	Approved
0.6872	Remote Similarity	NPD5026	Approved
0.6872	Remote Similarity	NPD4955	Approved
0.686	Remote Similarity	NPD919	Approved
0.6839	Remote Similarity	NPD8151	Discontinued
0.6831	Remote Similarity	NPD2342	Discontinued
0.6826	Remote Similarity	NPD7239	Suspended
0.6824	Remote Similarity	NPD1465	Phase 2
0.6816	Remote Similarity	NPD5030	Phase 2
0.6813	Remote Similarity	NPD8434	Phase 2
0.6813	Remote Similarity	NPD5038	Approved
0.6813	Remote Similarity	NPD5037	Approved
0.6795	Remote Similarity	NPD7008	Discontinued
0.6792	Remote Similarity	NPD6651	Approved
0.6789	Remote Similarity	NPD6823	Phase 2
0.6772	Remote Similarity	NPD2979	Phase 3
0.6766	Remote Similarity	NPD920	Approved
0.6758	Remote Similarity	NPD5036	Approved
0.6755	Remote Similarity	NPD3026	Approved
0.6755	Remote Similarity	NPD3023	Approved
0.6747	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5710	Approved
0.6743	Remote Similarity	NPD5711	Approved
0.6738	Remote Similarity	NPD1237	Approved
0.6733	Remote Similarity	NPD3025	Approved
0.6733	Remote Similarity	NPD1651	Approved
0.6733	Remote Similarity	NPD3024	Approved
0.673	Remote Similarity	NPD230	Phase 1
0.6728	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD8455	Phase 2
0.6722	Remote Similarity	NPD5027	Approved
0.6722	Remote Similarity	NPD5031	Approved
0.6722	Remote Similarity	NPD5029	Approved
0.6713	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7635	Approved
0.6711	Remote Similarity	NPD1281	Approved
0.671	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3400	Discontinued
0.6688	Remote Similarity	NPD1876	Approved
0.6686	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7799	Discontinued
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD5968	Phase 3
0.6667	Remote Similarity	NPD6100	Approved
0.6648	Remote Similarity	NPD7229	Phase 3
0.6648	Remote Similarity	NPD5035	Approved
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD1243	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