NPASS Compound

Structure

NPC475718 OpenBabel07101718192D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 -5.1962 3.0000 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 2.5000 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 1.7321 3.0000 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 -2.5981 -1.5000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -6.0622 2.5000 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 2.5000 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 -2.5981 1.5000 0.0000 C 0 0 3 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -5.1962 -2.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 35 1 0 0 0 0 5 7 1 0 0 0 0 5 17 2 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 36 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 17 23 1 0 0 0 0 18 31 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 28 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 26 1 0 0 0 0 23 29 2 0 0 0 0 24 25 2 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 26 33 2 0 0 0 0 27 29 1 0 0 0 0 27 34 2 0 0 0 0 28 36 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.18
Volume:	505.808
LogP:	5.45
LogD:	3.471
LogS:	-3.571
# Rotatable Bonds:	7
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.126
Synthetic Accessibility Score:	3.22
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.154
MDCK Permeability:	8.98936741577927e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.318
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	96.48494720458984%
Volume Distribution (VD):	0.3
Pgp-substrate:	5.72396993637085%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.566
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.39
CYP2D6-substrate:	0.492
CYP3A4-inhibitor:	0.142
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	5.482
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.697
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.427
Skin Sensitization:	0.941
Carcinogencity:	0.166
Eye Corrosion:	0.003
Eye Irritation:	0.898
Respiratory Toxicity:	0.288

Download Data

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

Natural Product: NPC475718

Natural Product ID:	NPC475718
*Common Name:**	Arenarin B
IUPAC Name:	7-hydroxy-8-[(E)-4-hydroxy-3-methylbut-2-enoxy]-2-(4-hydroxyphenyl)-3-methoxy-10-prop-1-en-2-yl-9,10-dihydrophenanthrene-1,4-dione
Synonyms:
Standard InCHIKey:	JDFIMWOTNMEMEF-LFIBNONCSA-N
Standard InCHI:	InChI=1S/C29H28O7/c1-15(2)20-13-21-19(9-10-22(32)28(21)36-12-11-16(3)14-30)24-25(20)26(33)23(29(35-4)27(24)34)17-5-7-18(31)8-6-17/h5-11,20,30-32H,1,12-14H2,2-4H3/b16-11+
SMILES:	CC(=C)C1CC2=C(C=CC(=C2OCC=C(C)CO)O)C3=C1C(=O)C(=C(C3=O)OC)C4=CC=C(C=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512540
PubChem CID:	44575465
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	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
GI50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4733	Organism	Carpophilus	Carpophilus	Activity	=	20.0	%	PMID[517533]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3.8	ug.mL-1	PMID[517533]

☑ 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 NPC475718 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	372
0.1-0.2	1413
0.2-0.3	3399
0.3-0.4	8429
0.4-0.5	10170
0.5-0.6	3518
0.6-0.7	6908
0.7-0.8	7942
0.8-0.85	505
0.85-0.9	36
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC474556
0.902	High Similarity	NPC288353
0.9007	High Similarity	NPC472838
0.9007	High Similarity	NPC306011
0.8867	High Similarity	NPC58373
0.8816	High Similarity	NPC58310
0.8816	High Similarity	NPC295977
0.8784	High Similarity	NPC192597
0.8784	High Similarity	NPC141817
0.8784	High Similarity	NPC229218
0.8784	High Similarity	NPC169214
0.8784	High Similarity	NPC176030
0.8776	High Similarity	NPC78987
0.8776	High Similarity	NPC82336
0.8758	High Similarity	NPC144283
0.8688	High Similarity	NPC263212
0.8639	High Similarity	NPC284409
0.8627	High Similarity	NPC472837
0.8611	High Similarity	NPC239302
0.859	High Similarity	NPC478159
0.859	High Similarity	NPC478161
0.858	High Similarity	NPC188079
0.8562	High Similarity	NPC472839
0.8543	High Similarity	NPC472836
0.8497	Intermediate Similarity	NPC77598
0.8494	Intermediate Similarity	NPC47191
0.8491	Intermediate Similarity	NPC472962
0.8491	Intermediate Similarity	NPC472961
0.8487	Intermediate Similarity	NPC160777
0.8487	Intermediate Similarity	NPC73416
0.8477	Intermediate Similarity	NPC224884
0.8477	Intermediate Similarity	NPC209085
0.8472	Intermediate Similarity	NPC172673
0.8462	Intermediate Similarity	NPC226661
0.8462	Intermediate Similarity	NPC164912
0.8457	Intermediate Similarity	NPC477517
0.8447	Intermediate Similarity	NPC134047
0.8447	Intermediate Similarity	NPC173729
0.8447	Intermediate Similarity	NPC223006
0.8447	Intermediate Similarity	NPC272750
0.8443	Intermediate Similarity	NPC244903
0.8442	Intermediate Similarity	NPC237904
0.8431	Intermediate Similarity	NPC39361
0.8428	Intermediate Similarity	NPC245891
0.8428	Intermediate Similarity	NPC104876
0.8421	Intermediate Similarity	NPC196941
0.8421	Intermediate Similarity	NPC309169
0.8411	Intermediate Similarity	NPC11314
0.8408	Intermediate Similarity	NPC474000
0.84	Intermediate Similarity	NPC29599
0.8397	Intermediate Similarity	NPC115869
0.8397	Intermediate Similarity	NPC118427
0.8395	Intermediate Similarity	NPC475888
0.8395	Intermediate Similarity	NPC303174
0.8385	Intermediate Similarity	NPC211107
0.8385	Intermediate Similarity	NPC144557
0.8377	Intermediate Similarity	NPC52692
0.8375	Intermediate Similarity	NPC36217
0.8375	Intermediate Similarity	NPC287328
0.8375	Intermediate Similarity	NPC472902
0.8375	Intermediate Similarity	NPC474960
0.8375	Intermediate Similarity	NPC282009
0.8365	Intermediate Similarity	NPC471479
0.8365	Intermediate Similarity	NPC471515
0.8355	Intermediate Similarity	NPC239608
0.8355	Intermediate Similarity	NPC46161
0.8354	Intermediate Similarity	NPC56786
0.8354	Intermediate Similarity	NPC300757
0.8354	Intermediate Similarity	NPC180901
0.8354	Intermediate Similarity	NPC268008
0.8354	Intermediate Similarity	NPC80534
0.8344	Intermediate Similarity	NPC43319
0.8344	Intermediate Similarity	NPC260979
0.8344	Intermediate Similarity	NPC131121
0.8344	Intermediate Similarity	NPC84273
0.8344	Intermediate Similarity	NPC472912
0.8333	Intermediate Similarity	NPC186686
0.8333	Intermediate Similarity	NPC322021
0.8333	Intermediate Similarity	NPC474240
0.8333	Intermediate Similarity	NPC473579
0.8333	Intermediate Similarity	NPC472625
0.8333	Intermediate Similarity	NPC475454
0.8333	Intermediate Similarity	NPC475311
0.8333	Intermediate Similarity	NPC473680
0.8333	Intermediate Similarity	NPC118033
0.8323	Intermediate Similarity	NPC471499
0.8323	Intermediate Similarity	NPC472906
0.8322	Intermediate Similarity	NPC90128
0.8322	Intermediate Similarity	NPC303680
0.8322	Intermediate Similarity	NPC84076
0.8313	Intermediate Similarity	NPC22192
0.8313	Intermediate Similarity	NPC280680
0.8313	Intermediate Similarity	NPC477410
0.8312	Intermediate Similarity	NPC223592
0.8311	Intermediate Similarity	NPC95485
0.8311	Intermediate Similarity	NPC89504
0.8311	Intermediate Similarity	NPC22644
0.8311	Intermediate Similarity	NPC88065
0.8303	Intermediate Similarity	NPC102277
0.8303	Intermediate Similarity	NPC279209
0.8302	Intermediate Similarity	NPC13858
0.8302	Intermediate Similarity	NPC326037
0.8302	Intermediate Similarity	NPC320825
0.8302	Intermediate Similarity	NPC153512
0.8302	Intermediate Similarity	NPC471500
0.8302	Intermediate Similarity	NPC213401
0.8301	Intermediate Similarity	NPC308006
0.8301	Intermediate Similarity	NPC91694
0.8301	Intermediate Similarity	NPC300603
0.8293	Intermediate Similarity	NPC469521
0.8293	Intermediate Similarity	NPC474024
0.8293	Intermediate Similarity	NPC218226
0.8293	Intermediate Similarity	NPC476306
0.8291	Intermediate Similarity	NPC472905
0.8291	Intermediate Similarity	NPC236223
0.8291	Intermediate Similarity	NPC305710
0.8291	Intermediate Similarity	NPC179126
0.8291	Intermediate Similarity	NPC475770
0.8291	Intermediate Similarity	NPC270620
0.8291	Intermediate Similarity	NPC78326
0.8291	Intermediate Similarity	NPC469550
0.8289	Intermediate Similarity	NPC201297
0.8282	Intermediate Similarity	NPC62261
0.8282	Intermediate Similarity	NPC293319
0.828	Intermediate Similarity	NPC473773
0.828	Intermediate Similarity	NPC302783
0.828	Intermediate Similarity	NPC473201
0.828	Intermediate Similarity	NPC475579
0.828	Intermediate Similarity	NPC78505
0.828	Intermediate Similarity	NPC75377
0.8276	Intermediate Similarity	NPC304622
0.8272	Intermediate Similarity	NPC474150
0.8272	Intermediate Similarity	NPC472964
0.8272	Intermediate Similarity	NPC149389
0.8272	Intermediate Similarity	NPC474162
0.8272	Intermediate Similarity	NPC201800
0.8269	Intermediate Similarity	NPC237441
0.8264	Intermediate Similarity	NPC123228
0.8264	Intermediate Similarity	NPC123722
0.8264	Intermediate Similarity	NPC151167
0.8264	Intermediate Similarity	NPC276466
0.8264	Intermediate Similarity	NPC5018
0.8261	Intermediate Similarity	NPC471973
0.8261	Intermediate Similarity	NPC470326
0.8261	Intermediate Similarity	NPC321399
0.8261	Intermediate Similarity	NPC470183
0.8253	Intermediate Similarity	NPC4200
0.8252	Intermediate Similarity	NPC53305
0.8252	Intermediate Similarity	NPC9067
0.8252	Intermediate Similarity	NPC257589
0.8252	Intermediate Similarity	NPC3221
0.825	Intermediate Similarity	NPC299520
0.825	Intermediate Similarity	NPC472963
0.825	Intermediate Similarity	NPC67876
0.825	Intermediate Similarity	NPC273843
0.825	Intermediate Similarity	NPC472598
0.825	Intermediate Similarity	NPC129684
0.825	Intermediate Similarity	NPC136674
0.825	Intermediate Similarity	NPC474055
0.825	Intermediate Similarity	NPC52530
0.8247	Intermediate Similarity	NPC225351
0.8242	Intermediate Similarity	NPC41494
0.8242	Intermediate Similarity	NPC476637
0.8242	Intermediate Similarity	NPC216403
0.8242	Intermediate Similarity	NPC186100
0.8239	Intermediate Similarity	NPC67396
0.8239	Intermediate Similarity	NPC133392
0.8235	Intermediate Similarity	NPC50954
0.8232	Intermediate Similarity	NPC470462
0.8232	Intermediate Similarity	NPC471213
0.8231	Intermediate Similarity	NPC312560
0.8228	Intermediate Similarity	NPC82325
0.8228	Intermediate Similarity	NPC60211
0.8228	Intermediate Similarity	NPC279989
0.8228	Intermediate Similarity	NPC28103
0.8224	Intermediate Similarity	NPC472410
0.8221	Intermediate Similarity	NPC476295
0.8221	Intermediate Similarity	NPC7483
0.8221	Intermediate Similarity	NPC470459
0.8219	Intermediate Similarity	NPC319282
0.8219	Intermediate Similarity	NPC215941
0.8219	Intermediate Similarity	NPC65935
0.8219	Intermediate Similarity	NPC311419
0.8219	Intermediate Similarity	NPC137427
0.8219	Intermediate Similarity	NPC66905
0.8219	Intermediate Similarity	NPC275724
0.8219	Intermediate Similarity	NPC244246
0.8219	Intermediate Similarity	NPC123196
0.8212	Intermediate Similarity	NPC474784
0.821	Intermediate Similarity	NPC26326
0.821	Intermediate Similarity	NPC318081
0.821	Intermediate Similarity	NPC173137
0.821	Intermediate Similarity	NPC474239
0.821	Intermediate Similarity	NPC278427
0.821	Intermediate Similarity	NPC289771
0.821	Intermediate Similarity	NPC472632
0.821	Intermediate Similarity	NPC474038
0.8207	Intermediate Similarity	NPC307050
0.8207	Intermediate Similarity	NPC277458
0.82	Intermediate Similarity	NPC264022

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 NPC475718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	931
0.2-0.3	1498
0.3-0.4	2547
0.4-0.5	1983
0.5-0.6	1023
0.6-0.7	666
0.7-0.8	162
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
0.8231	Intermediate Similarity	NPD4060	Phase 1
0.8187	Intermediate Similarity	NPD3882	Suspended
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8113	Intermediate Similarity	NPD1934	Approved
0.8063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2801	Approved
0.7933	Intermediate Similarity	NPD6355	Discontinued
0.7917	Intermediate Similarity	NPD5844	Phase 1
0.7901	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD8166	Discontinued
0.7862	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6798	Discontinued
0.7848	Intermediate Similarity	NPD1512	Approved
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7803	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1511	Approved
0.7706	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7673	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7661	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD7028	Phase 2
0.7651	Intermediate Similarity	NPD9494	Approved
0.7647	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD3620	Phase 2
0.7632	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD2488	Approved
0.7627	Intermediate Similarity	NPD2490	Approved
0.7625	Intermediate Similarity	NPD6273	Approved
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5494	Approved
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7593	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5762	Approved
0.7564	Intermediate Similarity	NPD5763	Approved
0.7561	Intermediate Similarity	NPD6801	Discontinued
0.756	Intermediate Similarity	NPD8127	Discontinued
0.755	Intermediate Similarity	NPD7095	Approved
0.7546	Intermediate Similarity	NPD6599	Discontinued
0.7546	Intermediate Similarity	NPD4380	Phase 2
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3750	Approved
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7515	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6190	Approved
0.747	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7455	Intermediate Similarity	NPD37	Approved
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7451	Intermediate Similarity	NPD6233	Phase 2
0.745	Intermediate Similarity	NPD1283	Approved
0.7442	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4966	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7421	Intermediate Similarity	NPD7003	Approved
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.7405	Intermediate Similarity	NPD3057	Approved
0.7405	Intermediate Similarity	NPD2491	Approved
0.7403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1613	Approved
0.74	Intermediate Similarity	NPD2797	Approved
0.7397	Intermediate Similarity	NPD1651	Approved
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7381	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5536	Phase 2
0.7358	Intermediate Similarity	NPD6674	Discontinued
0.7346	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5283	Phase 1
0.7342	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1471	Phase 3
0.7342	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD4062	Phase 3
0.7329	Intermediate Similarity	NPD3300	Phase 2
0.732	Intermediate Similarity	NPD3027	Phase 3
0.7315	Intermediate Similarity	NPD1608	Approved
0.7312	Intermediate Similarity	NPD3448	Approved
0.7312	Intermediate Similarity	NPD2972	Approved
0.7312	Intermediate Similarity	NPD3533	Approved
0.7296	Intermediate Similarity	NPD1549	Phase 2
0.7293	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2979	Phase 3
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7278	Intermediate Similarity	NPD2438	Suspended
0.7278	Intermediate Similarity	NPD4476	Approved
0.7278	Intermediate Similarity	NPD4477	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD5402	Approved
0.7258	Intermediate Similarity	NPD2494	Approved
0.7258	Intermediate Similarity	NPD2493	Approved
0.7256	Intermediate Similarity	NPD5403	Approved
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1281	Approved
0.7239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD919	Approved
0.7234	Intermediate Similarity	NPD4583	Approved
0.7234	Intermediate Similarity	NPD4582	Approved
0.723	Intermediate Similarity	NPD4626	Approved
0.723	Intermediate Similarity	NPD2932	Approved
0.7226	Intermediate Similarity	NPD8032	Phase 2
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7215	Intermediate Similarity	NPD1510	Phase 2
0.7215	Intermediate Similarity	NPD3748	Approved
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7195	Intermediate Similarity	NPD5049	Phase 3
0.7191	Intermediate Similarity	NPD2971	Approved
0.7191	Intermediate Similarity	NPD8312	Approved
0.7191	Intermediate Similarity	NPD8313	Approved
0.7191	Intermediate Similarity	NPD2968	Approved
0.719	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2897	Discontinued
0.7188	Intermediate Similarity	NPD4534	Discontinued
0.7188	Intermediate Similarity	NPD5958	Discontinued
0.7188	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7411	Suspended
0.7181	Intermediate Similarity	NPD4002	Approved
0.7181	Intermediate Similarity	NPD4004	Approved
0.7179	Intermediate Similarity	NPD4140	Approved
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7171	Intermediate Similarity	NPD3266	Approved
0.7171	Intermediate Similarity	NPD3267	Approved
0.717	Intermediate Similarity	NPD2796	Approved
0.7168	Intermediate Similarity	NPD3926	Phase 2
0.7166	Intermediate Similarity	NPD3450	Approved
0.7166	Intermediate Similarity	NPD3452	Approved
0.7162	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD3887	Approved
0.7151	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD447	Suspended
0.7134	Intermediate Similarity	NPD5735	Approved
0.7134	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD27	Approved
0.7126	Intermediate Similarity	NPD2489	Approved
0.7124	Intermediate Similarity	NPD2798	Approved
0.7114	Intermediate Similarity	NPD17	Approved
0.7114	Intermediate Similarity	NPD3019	Approved
0.7107	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8651	Approved
0.7105	Intermediate Similarity	NPD1876	Approved
0.7098	Intermediate Similarity	NPD5676	Approved
0.7093	Intermediate Similarity	NPD4666	Phase 3
0.7089	Intermediate Similarity	NPD1607	Approved
0.7081	Intermediate Similarity	NPD2424	Discontinued
0.7079	Intermediate Similarity	NPD6559	Discontinued
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.707	Intermediate Similarity	NPD943	Approved
0.707	Intermediate Similarity	NPD1240	Approved
0.7066	Intermediate Similarity	NPD2649	Approved
0.7066	Intermediate Similarity	NPD2651	Approved
0.7063	Intermediate Similarity	NPD2531	Phase 2
0.7063	Intermediate Similarity	NPD3022	Approved
0.7063	Intermediate Similarity	NPD3021	Approved
0.7059	Intermediate Similarity	NPD5977	Approved
0.7059	Intermediate Similarity	NPD5978	Approved
0.7053	Intermediate Similarity	NPD4040	Phase 1
0.7051	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD7427	Discontinued
0.7048	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7177	Discontinued
0.7045	Intermediate Similarity	NPD2163	Approved
0.7043	Intermediate Similarity	NPD2975	Approved
0.7043	Intermediate Similarity	NPD2973	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