NPASS Compound

Structure

NPC471448 OpenBabel07101718202D 30 33 0 0 1 0 0 0 0 0999 V2000 1.6750 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2926 0.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7103 -0.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1100 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6993 -0.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1170 -0.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2981 0.7420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 -0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1115 -1.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 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 2.8913 1.6555 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8968 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -4.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 -1.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5183 -1.9986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4791 2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4901 2.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 12 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 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	401.13
Volume:	412.745
LogP:	3.461
LogD:	2.379
LogS:	-4.038
# Rotatable Bonds:	5
TPSA:	102.92
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	3.012
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:	-4.797
MDCK Permeability:	5.734597834816668e-06
Pgp-inhibitor:	0.247
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.27
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	96.15180969238281%
Volume Distribution (VD):	0.525
Pgp-substrate:	2.9814789295196533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.82
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.742
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.557

ADMET: Excretion

Clearance (CL):	7.48
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.32
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC471448

Natural Product ID:	NPC471448
*Common Name:**	7-(R/S)-Hydroxylamellarin A
IUPAC Name:	1-[3,4-bis(4-hydroxyphenyl)pyrrol-1-yl]-2-hydroxy-2-(4-hydroxyphenyl)ethanone
Synonyms:	7-(R/S)-Hydroxylamellarin A
Standard InCHIKey:	RYIBSKICTMDCHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H19NO5/c26-18-7-1-15(2-8-18)21-13-25(14-22(21)16-3-9-19(27)10-4-16)24(30)23(29)17-5-11-20(28)12-6-17/h1-14,23,26-29H
SMILES:	C1=CC(=CC=C1C2=CN(C=C2C3=CC=C(C=C3)O)C(=O)C(C4=CC=C(C=C4)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249453
PubChem CID:	24179494
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
IC50	2
Others	6

Activity Type	# Activity
Cell Line	5
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[545027]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	87.0	%	PMID[545027]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	33.0	%	PMID[545027]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	-8.0	%	PMID[545027]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	34.0	%	PMID[545027]
NPT2	Others	Unspecified		IC50	=	1900.0	nM	PMID[545027]
NPT2	Others	Unspecified		Inhibition	=	98.0	%	PMID[545027]
NPT2	Others	Unspecified		IC50	=	3700.0	nM	PMID[545027]

☑ 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 NPC471448 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	338
0.1-0.2	1710
0.2-0.3	9590
0.3-0.4	7735
0.4-0.5	15986
0.5-0.6	5711
0.6-0.7	1523
0.7-0.8	102
0.8-0.85	0
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	NPC271792
0.7672	Intermediate Similarity	NPC295158
0.7638	Intermediate Similarity	NPC210256
0.7628	Intermediate Similarity	NPC285343
0.7619	Intermediate Similarity	NPC319232
0.7619	Intermediate Similarity	NPC24370
0.7594	Intermediate Similarity	NPC326363
0.757	Intermediate Similarity	NPC323752
0.755	Intermediate Similarity	NPC470500
0.7548	Intermediate Similarity	NPC14686
0.7546	Intermediate Similarity	NPC28945
0.7526	Intermediate Similarity	NPC56170
0.7513	Intermediate Similarity	NPC127085
0.75	Intermediate Similarity	NPC269270
0.7488	Intermediate Similarity	NPC220852
0.7488	Intermediate Similarity	NPC61038
0.7454	Intermediate Similarity	NPC325976
0.7426	Intermediate Similarity	NPC175602
0.7416	Intermediate Similarity	NPC315804
0.7416	Intermediate Similarity	NPC313804
0.7374	Intermediate Similarity	NPC473814
0.7374	Intermediate Similarity	NPC78767
0.736	Intermediate Similarity	NPC93390
0.7343	Intermediate Similarity	NPC207866
0.7337	Intermediate Similarity	NPC472284
0.7313	Intermediate Similarity	NPC155792
0.7306	Intermediate Similarity	NPC184225
0.7304	Intermediate Similarity	NPC88008
0.7282	Intermediate Similarity	NPC124086
0.7273	Intermediate Similarity	NPC146724
0.7256	Intermediate Similarity	NPC186351
0.725	Intermediate Similarity	NPC102008
0.7245	Intermediate Similarity	NPC3715
0.7241	Intermediate Similarity	NPC53144
0.7238	Intermediate Similarity	NPC246658
0.7236	Intermediate Similarity	NPC473053
0.7216	Intermediate Similarity	NPC241025
0.7212	Intermediate Similarity	NPC110182
0.7204	Intermediate Similarity	NPC264285
0.7204	Intermediate Similarity	NPC471178
0.72	Intermediate Similarity	NPC74153
0.7189	Intermediate Similarity	NPC59779
0.7189	Intermediate Similarity	NPC471177
0.7189	Intermediate Similarity	NPC124542
0.7172	Intermediate Similarity	NPC99666
0.7164	Intermediate Similarity	NPC149708
0.7143	Intermediate Similarity	NPC239763
0.7143	Intermediate Similarity	NPC190401
0.7136	Intermediate Similarity	NPC473821
0.7135	Intermediate Similarity	NPC164340
0.713	Intermediate Similarity	NPC214142
0.7123	Intermediate Similarity	NPC321592
0.7123	Intermediate Similarity	NPC54803
0.7115	Intermediate Similarity	NPC5145
0.711	Intermediate Similarity	NPC223409
0.7108	Intermediate Similarity	NPC470678
0.7108	Intermediate Similarity	NPC211813
0.7103	Intermediate Similarity	NPC473317
0.7103	Intermediate Similarity	NPC121069
0.7097	Intermediate Similarity	NPC261251
0.7087	Intermediate Similarity	NPC472286
0.7087	Intermediate Similarity	NPC472287
0.7085	Intermediate Similarity	NPC324149
0.7079	Intermediate Similarity	NPC212213
0.7075	Intermediate Similarity	NPC268393
0.7075	Intermediate Similarity	NPC13599
0.7075	Intermediate Similarity	NPC303384
0.7075	Intermediate Similarity	NPC3214
0.7075	Intermediate Similarity	NPC191088
0.7075	Intermediate Similarity	NPC27041
0.7075	Intermediate Similarity	NPC298840
0.707	Intermediate Similarity	NPC16352
0.7064	Intermediate Similarity	NPC100547
0.7053	Intermediate Similarity	NPC252590
0.7048	Intermediate Similarity	NPC219087
0.7043	Intermediate Similarity	NPC314882
0.7033	Intermediate Similarity	NPC85273
0.7032	Intermediate Similarity	NPC322135
0.7032	Intermediate Similarity	NPC95240
0.7027	Intermediate Similarity	NPC477549
0.702	Intermediate Similarity	NPC44354
0.7018	Intermediate Similarity	NPC304307
0.7018	Intermediate Similarity	NPC118559
0.7018	Intermediate Similarity	NPC34580
0.7018	Intermediate Similarity	NPC124920
0.7014	Intermediate Similarity	NPC323198
0.701	Intermediate Similarity	NPC213308
0.701	Intermediate Similarity	NPC471997
0.701	Intermediate Similarity	NPC315491
0.701	Intermediate Similarity	NPC45459
0.7005	Intermediate Similarity	NPC125597
0.7	Intermediate Similarity	NPC14288
0.6991	Remote Similarity	NPC470501
0.699	Remote Similarity	NPC200836
0.699	Remote Similarity	NPC207851
0.699	Remote Similarity	NPC475774
0.6984	Remote Similarity	NPC108469
0.6981	Remote Similarity	NPC478157
0.6971	Remote Similarity	NPC183777
0.6968	Remote Similarity	NPC97367
0.6968	Remote Similarity	NPC473057
0.6964	Remote Similarity	NPC474183
0.6957	Remote Similarity	NPC118832
0.6957	Remote Similarity	NPC47059
0.6957	Remote Similarity	NPC264166
0.6957	Remote Similarity	NPC274291
0.6957	Remote Similarity	NPC165349
0.6957	Remote Similarity	NPC329708
0.695	Remote Similarity	NPC473763
0.695	Remote Similarity	NPC117244
0.6946	Remote Similarity	NPC156704
0.6944	Remote Similarity	NPC470502
0.6943	Remote Similarity	NPC203754
0.6943	Remote Similarity	NPC150048
0.6923	Remote Similarity	NPC478006
0.6916	Remote Similarity	NPC75179
0.6914	Remote Similarity	NPC473360
0.6912	Remote Similarity	NPC474916
0.6912	Remote Similarity	NPC239954
0.6898	Remote Similarity	NPC54066
0.6898	Remote Similarity	NPC276657
0.6893	Remote Similarity	NPC300183
0.689	Remote Similarity	NPC316403
0.6884	Remote Similarity	NPC46580
0.6881	Remote Similarity	NPC470503
0.6872	Remote Similarity	NPC248462
0.6869	Remote Similarity	NPC62510
0.6869	Remote Similarity	NPC322064
0.6866	Remote Similarity	NPC253314
0.6862	Remote Similarity	NPC478009
0.6861	Remote Similarity	NPC284888
0.6857	Remote Similarity	NPC171787
0.6853	Remote Similarity	NPC153400
0.6834	Remote Similarity	NPC171171
0.683	Remote Similarity	NPC245055
0.683	Remote Similarity	NPC33064
0.6829	Remote Similarity	NPC168911
0.6823	Remote Similarity	NPC314940
0.6823	Remote Similarity	NPC473764
0.6822	Remote Similarity	NPC237740
0.6821	Remote Similarity	NPC64436
0.6814	Remote Similarity	NPC470784
0.681	Remote Similarity	NPC193238
0.681	Remote Similarity	NPC53344
0.6808	Remote Similarity	NPC111732
0.6806	Remote Similarity	NPC314270
0.6804	Remote Similarity	NPC139763
0.6802	Remote Similarity	NPC470474
0.6798	Remote Similarity	NPC329541
0.6796	Remote Similarity	NPC160127
0.6796	Remote Similarity	NPC50997
0.6794	Remote Similarity	NPC475070
0.6794	Remote Similarity	NPC472259
0.6792	Remote Similarity	NPC470020
0.6791	Remote Similarity	NPC74969
0.6784	Remote Similarity	NPC314002
0.678	Remote Similarity	NPC227582
0.678	Remote Similarity	NPC90229
0.678	Remote Similarity	NPC77555
0.6776	Remote Similarity	NPC236668
0.6776	Remote Similarity	NPC316181
0.6776	Remote Similarity	NPC74562
0.6776	Remote Similarity	NPC151781
0.677	Remote Similarity	NPC15801
0.6768	Remote Similarity	NPC220765
0.6759	Remote Similarity	NPC472285
0.6756	Remote Similarity	NPC253675
0.6754	Remote Similarity	NPC210296
0.6754	Remote Similarity	NPC99891
0.675	Remote Similarity	NPC94752
0.675	Remote Similarity	NPC315555
0.675	Remote Similarity	NPC315467
0.6749	Remote Similarity	NPC133140
0.6749	Remote Similarity	NPC195268
0.6745	Remote Similarity	NPC162860
0.6745	Remote Similarity	NPC478158
0.6745	Remote Similarity	NPC174758
0.6744	Remote Similarity	NPC146976
0.674	Remote Similarity	NPC82472
0.6739	Remote Similarity	NPC78609
0.6737	Remote Similarity	NPC191863
0.6737	Remote Similarity	NPC289776
0.6737	Remote Similarity	NPC133470
0.6734	Remote Similarity	NPC204717
0.6729	Remote Similarity	NPC202605
0.6729	Remote Similarity	NPC75634
0.6729	Remote Similarity	NPC112206
0.6728	Remote Similarity	NPC281049
0.6728	Remote Similarity	NPC303658
0.6722	Remote Similarity	NPC478010
0.6722	Remote Similarity	NPC251439
0.6718	Remote Similarity	NPC469938
0.6716	Remote Similarity	NPC198673
0.6716	Remote Similarity	NPC289786
0.6714	Remote Similarity	NPC11464
0.6713	Remote Similarity	NPC330009
0.6712	Remote Similarity	NPC244536
0.6703	Remote Similarity	NPC233702
0.6701	Remote Similarity	NPC158129
0.6699	Remote Similarity	NPC328318

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 NPC471448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	600
0.2-0.3	735
0.3-0.4	1132
0.4-0.5	2876
0.5-0.6	2968
0.6-0.7	609
0.7-0.8	19
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
0.7882	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7944	Discontinued
0.7513	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7948	Phase 1
0.7418	Intermediate Similarity	NPD2511	Approved
0.7393	Intermediate Similarity	NPD8356	Approved
0.7371	Intermediate Similarity	NPD7603	Discontinued
0.7363	Intermediate Similarity	NPD6975	Discontinued
0.7294	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6569	Phase 2
0.7256	Intermediate Similarity	NPD8430	Approved
0.725	Intermediate Similarity	NPD7778	Approved
0.725	Intermediate Similarity	NPD7777	Approved
0.725	Intermediate Similarity	NPD53	Approved
0.7219	Intermediate Similarity	NPD2781	Approved
0.7209	Intermediate Similarity	NPD7426	Phase 1
0.7204	Intermediate Similarity	NPD2782	Approved
0.7204	Intermediate Similarity	NPD2780	Approved
0.7189	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7001	Phase 3
0.7171	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3321	Discontinued
0.7129	Intermediate Similarity	NPD7069	Discontinued
0.7122	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8093	Discontinued
0.7041	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4923	Phase 1
0.701	Intermediate Similarity	NPD484	Approved
0.6995	Remote Similarity	NPD4989	Phase 2
0.698	Remote Similarity	NPD5512	Phase 3
0.6972	Remote Similarity	NPD5640	Discontinued
0.6971	Remote Similarity	NPD7453	Approved
0.6971	Remote Similarity	NPD7222	Phase 2
0.6971	Remote Similarity	NPD7452	Approved
0.697	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5088	Discontinued
0.6963	Remote Similarity	NPD6568	Discontinued
0.6961	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6999	Discontinued
0.6957	Remote Similarity	NPD4038	Approved
0.6957	Remote Similarity	NPD4035	Approved
0.6957	Remote Similarity	NPD32	Approved
0.6957	Remote Similarity	NPD4039	Approved
0.6957	Remote Similarity	NPD4033	Approved
0.6957	Remote Similarity	NPD31	Approved
0.6957	Remote Similarity	NPD4034	Approved
0.6957	Remote Similarity	NPD4036	Approved
0.6957	Remote Similarity	NPD4037	Approved
0.6957	Remote Similarity	NPD4122	Approved
0.6954	Remote Similarity	NPD4889	Approved
0.6941	Remote Similarity	NPD4845	Discontinued
0.6938	Remote Similarity	NPD2916	Discontinued
0.6938	Remote Similarity	NPD6376	Discontinued
0.6938	Remote Similarity	NPD7467	Discontinued
0.693	Remote Similarity	NPD6974	Phase 3
0.6923	Remote Similarity	NPD5898	Approved
0.6923	Remote Similarity	NPD5897	Approved
0.6923	Remote Similarity	NPD5899	Approved
0.6919	Remote Similarity	NPD7470	Discontinued
0.6919	Remote Similarity	NPD4375	Approved
0.6915	Remote Similarity	NPD6665	Discontinued
0.6903	Remote Similarity	NPD7576	Discontinued
0.69	Remote Similarity	NPD1213	Phase 3
0.6898	Remote Similarity	NPD7180	Phase 3
0.6895	Remote Similarity	NPD5823	Approved
0.689	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7878	Phase 2
0.6875	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8094	Discontinued
0.684	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4919	Phase 3
0.6834	Remote Similarity	NPD4921	Phase 3
0.6834	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4372	Phase 1
0.6828	Remote Similarity	NPD7417	Discontinued
0.6827	Remote Similarity	NPD5513	Phase 2
0.6822	Remote Similarity	NPD4897	Phase 2
0.6821	Remote Similarity	NPD6159	Phase 2
0.6811	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5255	Approved
0.6806	Remote Similarity	NPD3354	Phase 2
0.6804	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2383	Phase 1
0.6794	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5612	Discontinued
0.6786	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5601	Phase 2
0.676	Remote Similarity	NPD2896	Discontinued
0.6759	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3813	Approved
0.6754	Remote Similarity	NPD6790	Phase 1
0.6751	Remote Similarity	NPD6452	Discontinued
0.6749	Remote Similarity	NPD3921	Approved
0.6749	Remote Similarity	NPD3924	Approved
0.6749	Remote Similarity	NPD3923	Approved
0.6749	Remote Similarity	NPD3922	Approved
0.6743	Remote Similarity	NPD8479	Phase 2
0.6742	Remote Similarity	NPD3263	Phase 3
0.673	Remote Similarity	NPD5429	Discontinued
0.6728	Remote Similarity	NPD7395	Discontinued
0.6725	Remote Similarity	NPD6716	Phase 1
0.6725	Remote Similarity	NPD6517	Phase 3
0.6718	Remote Similarity	NPD5065	Approved
0.6717	Remote Similarity	NPD3386	Phase 2
0.6716	Remote Similarity	NPD6361	Phase 2
0.6716	Remote Similarity	NPD4948	Discontinued
0.6714	Remote Similarity	NPD5901	Discontinued
0.6714	Remote Similarity	NPD3392	Approved
0.6714	Remote Similarity	NPD6987	Phase 1
0.6714	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4086	Phase 1
0.6711	Remote Similarity	NPD7558	Phase 2
0.6711	Remote Similarity	NPD7885	Phase 2
0.6711	Remote Similarity	NPD7886	Phase 2
0.6702	Remote Similarity	NPD6026	Approved
0.6699	Remote Similarity	NPD1229	Phase 2
0.6698	Remote Similarity	NPD7665	Phase 2
0.6698	Remote Similarity	NPD7666	Phase 3
0.6695	Remote Similarity	NPD3809	Discontinued
0.6683	Remote Similarity	NPD7233	Approved
0.6683	Remote Similarity	NPD7234	Approved
0.6683	Remote Similarity	NPD3395	Approved
0.6683	Remote Similarity	NPD3396	Approved
0.6682	Remote Similarity	NPD6710	Phase 3
0.6682	Remote Similarity	NPD5559	Phase 2
0.6667	Remote Similarity	NPD7967	Discontinued
0.6667	Remote Similarity	NPD7011	Discontinued
0.6667	Remote Similarity	NPD6242	Discontinued
0.6653	Remote Similarity	NPD7655	Discontinued
0.6652	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3917	Approved
0.6651	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3918	Approved
0.6651	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6290	Phase 2
0.665	Remote Similarity	NPD8063	Discontinued
0.6638	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8016	Phase 3
0.6637	Remote Similarity	NPD7994	Phase 2
0.6636	Remote Similarity	NPD5507	Approved
0.6636	Remote Similarity	NPD5506	Approved
0.6635	Remote Similarity	NPD2177	Approved
0.6635	Remote Similarity	NPD2175	Phase 3
0.6635	Remote Similarity	NPD5426	Phase 3
0.6635	Remote Similarity	NPD2176	Approved
0.6635	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4551	Phase 2
0.6633	Remote Similarity	NPD9690	Approved
0.6632	Remote Similarity	NPD6283	Phase 2
0.6622	Remote Similarity	NPD6962	Phase 2
0.6621	Remote Similarity	NPD6500	Approved
0.6621	Remote Similarity	NPD6501	Approved
0.662	Remote Similarity	NPD3243	Approved
0.6617	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2123	Phase 3
0.661	Remote Similarity	NPD8370	Discontinued
0.6606	Remote Similarity	NPD6995	Phase 1
0.6605	Remote Similarity	NPD5939	Approved
0.6605	Remote Similarity	NPD5067	Phase 2
0.6605	Remote Similarity	NPD5066	Phase 2
0.6605	Remote Similarity	NPD5936	Approved
0.6605	Remote Similarity	NPD3915	Approved
0.6603	Remote Similarity	NPD6219	Discontinued
0.6603	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4418	Discontinued
0.6601	Remote Similarity	NPD4021	Phase 2
0.66	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5471	Phase 3
0.6598	Remote Similarity	NPD5862	Discovery
0.6597	Remote Similarity	NPD9705	Discontinued
0.6597	Remote Similarity	NPD112	Approved
0.6593	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD8289	Discontinued
0.659	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD9510	Approved
0.6582	Remote Similarity	NPD750	Phase 2
0.6582	Remote Similarity	NPD8246	Approved
0.6582	Remote Similarity	NPD8247	Approved
0.658	Remote Similarity	NPD925	Approved
0.658	Remote Similarity	NPD926	Approved
0.6579	Remote Similarity	NPD2582	Approved
0.6579	Remote Similarity	NPD7853	Phase 2
0.6579	Remote Similarity	NPD9383	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