NPASS Compound

Structure

NPC271792 OpenBabel07101718302D 29 32 0 0 0 0 0 0 0 0999 V2000 4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6810 -2.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2743 -3.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3080 -2.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 -0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 -3.6067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 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 2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 2.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1269 -4.5202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 0.4181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 16 2 0 0 0 0 2 8 2 0 0 0 0 2 16 1 0 0 0 0 3 9 1 0 0 0 0 3 17 2 0 0 0 0 4 10 2 0 0 0 0 4 17 1 0 0 0 0 5 11 1 0 0 0 0 5 18 2 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 24 25 1 0 0 0 0 24 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.13
Volume:	403.954
LogP:	4.398
LogD:	3.375
LogS:	-3.609
# Rotatable Bonds:	5
TPSA:	82.69
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	2.419
Fsp3:	0.042
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:	-4.745
MDCK Permeability:	8.217714821512345e-06
Pgp-inhibitor:	0.411
Pgp-substrate:	0.456
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.699
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	98.69957733154297%
Volume Distribution (VD):	0.512
Pgp-substrate:	1.2896114587783813%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.819
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.583
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.811
CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.777
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	14.004
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.496
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.726
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC271792

Natural Product ID:	NPC271792
*Common Name:**	Neolamellarin A
IUPAC Name:	1-[3,4-bis(4-hydroxyphenyl)pyrrol-1-yl]-2-(4-hydroxyphenyl)ethanone
Synonyms:
Standard InCHIKey:	ANCFAUCOYOMNJZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H19NO4/c26-19-7-1-16(2-8-19)13-24(29)25-14-22(17-3-9-20(27)10-4-17)23(15-25)18-5-11-21(28)12-6-18/h1-12,14-15,26-28H,13H2
SMILES:	Oc1ccc(cc1)CC(=O)n1cc(c(c1)c1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251656
PubChem CID:	24179369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles [CHEMONTID:0002695] Diphenylpyrroles

*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
NPO33428	dendrilla nigra	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17958397]

☑ 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
IC50	1
Others	3

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	20.0	%	PMID[500736]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	59500.0	nM	PMID[500737]
NPT2	Others	Unspecified		Inhibition	=	26.0	%	PMID[500736]
NPT2	Others	Unspecified		Activity	=	58.0	%	PMID[500736]
NPT2	Others	Unspecified		IC50	=	10800.0	nM	PMID[500737]

☑ 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 NPC271792 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	385
0.1-0.2	2433
0.2-0.3	12103
0.3-0.4	4972
0.4-0.5	15939
0.5-0.6	5144
0.6-0.7	1592
0.7-0.8	125
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC471448
0.7935	Intermediate Similarity	NPC56170
0.7876	Intermediate Similarity	NPC61038
0.7839	Intermediate Similarity	NPC14686
0.7812	Intermediate Similarity	NPC175602
0.7789	Intermediate Similarity	NPC269270
0.7766	Intermediate Similarity	NPC473814
0.7766	Intermediate Similarity	NPC78767
0.776	Intermediate Similarity	NPC210256
0.7754	Intermediate Similarity	NPC93390
0.7716	Intermediate Similarity	NPC207866
0.7707	Intermediate Similarity	NPC326363
0.7653	Intermediate Similarity	NPC124086
0.7632	Intermediate Similarity	NPC127085
0.7617	Intermediate Similarity	NPC53144
0.7614	Intermediate Similarity	NPC471178
0.7609	Intermediate Similarity	NPC295158
0.76	Intermediate Similarity	NPC471177
0.76	Intermediate Similarity	NPC124542
0.76	Intermediate Similarity	NPC59779
0.7579	Intermediate Similarity	NPC74153
0.7576	Intermediate Similarity	NPC110182
0.7571	Intermediate Similarity	NPC285343
0.7566	Intermediate Similarity	NPC146724
0.7562	Intermediate Similarity	NPC264285
0.7561	Intermediate Similarity	NPC24370
0.7561	Intermediate Similarity	NPC319232
0.756	Intermediate Similarity	NPC325976
0.7553	Intermediate Similarity	NPC99666
0.7513	Intermediate Similarity	NPC473821
0.75	Intermediate Similarity	NPC190401
0.75	Intermediate Similarity	NPC239763
0.7488	Intermediate Similarity	NPC28945
0.7474	Intermediate Similarity	NPC211813
0.746	Intermediate Similarity	NPC324149
0.7432	Intermediate Similarity	NPC164340
0.7429	Intermediate Similarity	NPC220852
0.7426	Intermediate Similarity	NPC27041
0.7426	Intermediate Similarity	NPC191088
0.7426	Intermediate Similarity	NPC246658
0.7426	Intermediate Similarity	NPC303384
0.7426	Intermediate Similarity	NPC268393
0.7426	Intermediate Similarity	NPC298840
0.7426	Intermediate Similarity	NPC13599
0.7426	Intermediate Similarity	NPC3214
0.7415	Intermediate Similarity	NPC16352
0.7387	Intermediate Similarity	NPC85273
0.7371	Intermediate Similarity	NPC213308
0.736	Intermediate Similarity	NPC473057
0.736	Intermediate Similarity	NPC97367
0.7347	Intermediate Similarity	NPC200836
0.7346	Intermediate Similarity	NPC323752
0.7306	Intermediate Similarity	NPC156704
0.7296	Intermediate Similarity	NPC470678
0.7282	Intermediate Similarity	NPC315491
0.7282	Intermediate Similarity	NPC45459
0.7282	Intermediate Similarity	NPC121069
0.7268	Intermediate Similarity	NPC315804
0.7268	Intermediate Similarity	NPC313804
0.7268	Intermediate Similarity	NPC474916
0.7249	Intermediate Similarity	NPC46580
0.7243	Intermediate Similarity	NPC248462
0.7233	Intermediate Similarity	NPC276657
0.7222	Intermediate Similarity	NPC470500
0.7211	Intermediate Similarity	NPC44354
0.7206	Intermediate Similarity	NPC322064
0.7196	Intermediate Similarity	NPC171171
0.719	Intermediate Similarity	NPC186351
0.7189	Intermediate Similarity	NPC64436
0.7182	Intermediate Similarity	NPC108469
0.7179	Intermediate Similarity	NPC472284
0.7165	Intermediate Similarity	NPC473053
0.7163	Intermediate Similarity	NPC184225
0.7157	Intermediate Similarity	NPC237740
0.7157	Intermediate Similarity	NPC155792
0.715	Intermediate Similarity	NPC88008
0.715	Intermediate Similarity	NPC329541
0.715	Intermediate Similarity	NPC183777
0.7143	Intermediate Similarity	NPC314002
0.7143	Intermediate Similarity	NPC241025
0.7136	Intermediate Similarity	NPC475070
0.7128	Intermediate Similarity	NPC77555
0.7128	Intermediate Similarity	NPC220765
0.7128	Intermediate Similarity	NPC90229
0.7115	Intermediate Similarity	NPC473317
0.7092	Intermediate Similarity	NPC102008
0.7091	Intermediate Similarity	NPC120251
0.709	Intermediate Similarity	NPC204717
0.7085	Intermediate Similarity	NPC475774
0.7083	Intermediate Similarity	NPC3715
0.7065	Intermediate Similarity	NPC252590
0.7047	Intermediate Similarity	NPC473763
0.7047	Intermediate Similarity	NPC117244
0.7044	Intermediate Similarity	NPC470020
0.7037	Intermediate Similarity	NPC477549
0.703	Intermediate Similarity	NPC171787
0.7024	Intermediate Similarity	NPC473360
0.7024	Intermediate Similarity	NPC236668
0.7014	Intermediate Similarity	NPC125597
0.7011	Intermediate Similarity	NPC473764
0.7011	Intermediate Similarity	NPC314940
0.701	Intermediate Similarity	NPC133140
0.701	Intermediate Similarity	NPC195268
0.7005	Intermediate Similarity	NPC96890
0.7005	Intermediate Similarity	NPC131887
0.7005	Intermediate Similarity	NPC184964
0.7005	Intermediate Similarity	NPC212213
0.6995	Remote Similarity	NPC174758
0.6991	Remote Similarity	NPC253675
0.699	Remote Similarity	NPC146976
0.6989	Remote Similarity	NPC139763
0.6981	Remote Similarity	NPC214142
0.698	Remote Similarity	NPC270918
0.698	Remote Similarity	NPC53344
0.6977	Remote Similarity	NPC200553
0.6977	Remote Similarity	NPC279189
0.6976	Remote Similarity	NPC112206
0.6976	Remote Similarity	NPC202605
0.6976	Remote Similarity	NPC219087
0.6965	Remote Similarity	NPC472259
0.6961	Remote Similarity	NPC11464
0.6961	Remote Similarity	NPC5145
0.6957	Remote Similarity	NPC330009
0.6954	Remote Similarity	NPC227582
0.6948	Remote Similarity	NPC304307
0.6948	Remote Similarity	NPC118559
0.6948	Remote Similarity	NPC261251
0.6948	Remote Similarity	NPC34580
0.6948	Remote Similarity	NPC124920
0.6942	Remote Similarity	NPC266931
0.6939	Remote Similarity	NPC276517
0.6935	Remote Similarity	NPC477019
0.6933	Remote Similarity	NPC153400
0.6931	Remote Similarity	NPC472286
0.6931	Remote Similarity	NPC471997
0.6931	Remote Similarity	NPC472287
0.6927	Remote Similarity	NPC94752
0.6927	Remote Similarity	NPC242923
0.6923	Remote Similarity	NPC191863
0.6923	Remote Similarity	NPC133470
0.6923	Remote Similarity	NPC289776
0.6919	Remote Similarity	NPC306376
0.6919	Remote Similarity	NPC220851
0.6916	Remote Similarity	NPC100547
0.6908	Remote Similarity	NPC478157
0.6903	Remote Similarity	NPC314882
0.6901	Remote Similarity	NPC214980
0.69	Remote Similarity	NPC31930
0.69	Remote Similarity	NPC300183
0.6898	Remote Similarity	NPC469938
0.6898	Remote Similarity	NPC207686
0.6897	Remote Similarity	NPC193238
0.6895	Remote Similarity	NPC470474
0.6893	Remote Similarity	NPC233702
0.6892	Remote Similarity	NPC78609
0.689	Remote Similarity	NPC204446
0.6884	Remote Similarity	NPC223409
0.6884	Remote Similarity	NPC95240
0.6884	Remote Similarity	NPC476578
0.6884	Remote Similarity	NPC322135
0.6884	Remote Similarity	NPC476582
0.6884	Remote Similarity	NPC4071
0.6881	Remote Similarity	NPC162002
0.6878	Remote Similarity	NPC213468
0.6866	Remote Similarity	NPC57398
0.6863	Remote Similarity	NPC82548
0.686	Remote Similarity	NPC271215
0.686	Remote Similarity	NPC149471
0.6852	Remote Similarity	NPC14288
0.685	Remote Similarity	NPC252338
0.6849	Remote Similarity	NPC15801
0.6845	Remote Similarity	NPC477976
0.6845	Remote Similarity	NPC471294
0.6842	Remote Similarity	NPC469727
0.6835	Remote Similarity	NPC174489
0.6834	Remote Similarity	NPC192315
0.6834	Remote Similarity	NPC239954
0.6833	Remote Similarity	NPC210296
0.6825	Remote Similarity	NPC54066
0.6823	Remote Similarity	NPC228835
0.6823	Remote Similarity	NPC207851
0.682	Remote Similarity	NPC54803
0.682	Remote Similarity	NPC321592
0.6816	Remote Similarity	NPC471944
0.6814	Remote Similarity	NPC313189
0.6811	Remote Similarity	NPC41717
0.681	Remote Similarity	NPC303658
0.6804	Remote Similarity	NPC278434
0.6802	Remote Similarity	NPC65408
0.6802	Remote Similarity	NPC198673
0.68	Remote Similarity	NPC476167
0.6798	Remote Similarity	NPC36229
0.6798	Remote Similarity	NPC476581
0.6798	Remote Similarity	NPC16452
0.6798	Remote Similarity	NPC285558
0.6796	Remote Similarity	NPC309845
0.6796	Remote Similarity	NPC290689
0.6794	Remote Similarity	NPC274982
0.6794	Remote Similarity	NPC469928
0.6794	Remote Similarity	NPC74969

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 NPC271792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	652
0.2-0.3	801
0.3-0.4	884
0.4-0.5	2833
0.5-0.6	2980
0.6-0.7	730
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8103	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7948	Phase 1
0.7627	Intermediate Similarity	NPD2781	Approved
0.7614	Intermediate Similarity	NPD2780	Approved
0.7614	Intermediate Similarity	NPD2782	Approved
0.7565	Intermediate Similarity	NPD6975	Discontinued
0.7561	Intermediate Similarity	NPD7603	Discontinued
0.7543	Intermediate Similarity	NPD2511	Approved
0.75	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7944	Discontinued
0.7429	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8356	Approved
0.7326	Intermediate Similarity	NPD4889	Approved
0.732	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6999	Discontinued
0.7286	Intermediate Similarity	NPD2916	Discontinued
0.7286	Intermediate Similarity	NPD6376	Discontinued
0.7283	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD484	Approved
0.7277	Intermediate Similarity	NPD6569	Phase 2
0.7273	Intermediate Similarity	NPD4845	Discontinued
0.7268	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7069	Discontinued
0.7228	Intermediate Similarity	NPD8093	Discontinued
0.72	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4923	Phase 1
0.7192	Intermediate Similarity	NPD8094	Discontinued
0.719	Intermediate Similarity	NPD8430	Approved
0.7186	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2896	Discontinued
0.7151	Intermediate Similarity	NPD3813	Approved
0.7151	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5601	Phase 2
0.71	Intermediate Similarity	NPD7001	Phase 3
0.7098	Intermediate Similarity	NPD6665	Discontinued
0.7092	Intermediate Similarity	NPD7778	Approved
0.7092	Intermediate Similarity	NPD7777	Approved
0.7092	Intermediate Similarity	NPD53	Approved
0.7083	Intermediate Similarity	NPD1213	Phase 3
0.7083	Intermediate Similarity	NPD3321	Discontinued
0.7081	Intermediate Similarity	NPD5065	Approved
0.7081	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5088	Discontinued
0.7068	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4948	Discontinued
0.7062	Intermediate Similarity	NPD7426	Phase 1
0.7053	Intermediate Similarity	NPD3354	Phase 2
0.705	Intermediate Similarity	NPD5901	Discontinued
0.703	Intermediate Similarity	NPD7665	Phase 2
0.703	Intermediate Similarity	NPD7666	Phase 3
0.7016	Intermediate Similarity	NPD4375	Approved
0.701	Intermediate Similarity	NPD3924	Approved
0.701	Intermediate Similarity	NPD3922	Approved
0.701	Intermediate Similarity	NPD3923	Approved
0.701	Intermediate Similarity	NPD3921	Approved
0.7005	Intermediate Similarity	NPD6159	Phase 2
0.7005	Intermediate Similarity	NPD6710	Phase 3
0.7005	Intermediate Similarity	NPD4989	Phase 2
0.7	Intermediate Similarity	NPD5513	Phase 2
0.7	Intermediate Similarity	NPD5255	Approved
0.6991	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5512	Phase 3
0.6986	Remote Similarity	NPD6790	Phase 1
0.698	Remote Similarity	NPD7222	Phase 2
0.698	Remote Similarity	NPD7452	Approved
0.698	Remote Similarity	NPD7453	Approved
0.6971	Remote Similarity	NPD6568	Discontinued
0.697	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5426	Phase 3
0.6952	Remote Similarity	NPD5471	Phase 3
0.6947	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7467	Discontinued
0.6943	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.694	Remote Similarity	NPD926	Approved
0.694	Remote Similarity	NPD925	Approved
0.6939	Remote Similarity	NPD4418	Discontinued
0.6931	Remote Similarity	NPD6452	Discontinued
0.6927	Remote Similarity	NPD7470	Discontinued
0.6923	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4372	Phase 1
0.6905	Remote Similarity	NPD7180	Phase 3
0.6905	Remote Similarity	NPD6242	Discontinued
0.6902	Remote Similarity	NPD5823	Approved
0.6893	Remote Similarity	NPD4852	Phase 2
0.6891	Remote Similarity	NPD6791	Phase 2
0.6888	Remote Similarity	NPD4551	Phase 2
0.6888	Remote Similarity	NPD6361	Phase 2
0.6881	Remote Similarity	NPD6987	Phase 1
0.6878	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5612	Discontinued
0.6875	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8016	Phase 3
0.6864	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3396	Approved
0.6853	Remote Similarity	NPD3395	Approved
0.6845	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD750	Phase 2
0.6844	Remote Similarity	NPD3809	Discontinued
0.6842	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5445	Approved
0.6837	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5505	Discontinued
0.6827	Remote Similarity	NPD4897	Phase 2
0.6825	Remote Similarity	NPD8479	Phase 2
0.6816	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3262	Approved
0.6816	Remote Similarity	NPD4511	Phase 1
0.6816	Remote Similarity	NPD6158	Phase 2
0.6811	Remote Similarity	NPD425	Approved
0.6811	Remote Similarity	NPD424	Approved
0.6809	Remote Similarity	NPD9690	Approved
0.6808	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3386	Phase 2
0.6804	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD201	Phase 2
0.6802	Remote Similarity	NPD200	Phase 2
0.6798	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3243	Approved
0.6777	Remote Similarity	NPD6974	Phase 3
0.6776	Remote Similarity	NPD9705	Discontinued
0.6776	Remote Similarity	NPD112	Approved
0.6774	Remote Similarity	NPD8106	Phase 2
0.6771	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7233	Approved
0.6769	Remote Similarity	NPD7234	Approved
0.6768	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5899	Approved
0.6754	Remote Similarity	NPD5897	Approved
0.6754	Remote Similarity	NPD5898	Approved
0.6753	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4919	Phase 3
0.6753	Remote Similarity	NPD4921	Phase 3
0.6744	Remote Similarity	NPD3263	Phase 3
0.6743	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6281	Approved
0.6732	Remote Similarity	NPD5429	Discontinued
0.6731	Remote Similarity	NPD3816	Phase 1
0.6731	Remote Similarity	NPD3815	Phase 1
0.6731	Remote Similarity	NPD5866	Approved
0.6731	Remote Similarity	NPD3917	Approved
0.6731	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3918	Approved
0.673	Remote Similarity	NPD7395	Discontinued
0.673	Remote Similarity	NPD7878	Phase 2
0.672	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD802	Phase 2
0.6717	Remote Similarity	NPD1038	Approved
0.6716	Remote Similarity	NPD3947	Discontinued
0.6716	Remote Similarity	NPD3397	Phase 2
0.6716	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7112	Discontinued
0.6713	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6026	Approved
0.6702	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3258	Approved
0.6696	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3229	Phase 2
0.6684	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4021	Phase 2
0.6684	Remote Similarity	NPD2092	Phase 2
0.6684	Remote Similarity	NPD6457	Approved
0.6684	Remote Similarity	NPD2094	Phase 2
0.6684	Remote Similarity	NPD2095	Phase 2
0.6683	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3915	Approved
0.6683	Remote Similarity	NPD6219	Discontinued
0.6682	Remote Similarity	NPD2813	Phase 3
0.6682	Remote Similarity	NPD7576	Discontinued
0.6682	Remote Similarity	NPD7417	Discontinued
0.6682	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7555	Discontinued
0.6681	Remote Similarity	NPD7923	Phase 2
0.6667	Remote Similarity	NPD4044	Discontinued
0.6667	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD5827	Discontinued
0.6652	Remote Similarity	NPD6716	Phase 1
0.6651	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7567	Approved
0.6651	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8493	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