NPASS Compound

Structure

NPC470746 OpenBabel07101718302D 43 46 0 0 1 0 0 0 0 0999 V2000 3.6026 -2.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2429 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7429 2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9839 0.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -1.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1603 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 -0.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8831 -2.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2648 1.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0738 2.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 2.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6921 -1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 5.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.6565 -0.0864 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.0617 -3.0501 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 2.5388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5216 0.8752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2817 3.9237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5727 -1.9522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5261 -0.8806 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 40 1 0 0 0 0 2 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 33 1 0 0 0 0 6 41 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 3 0 0 0 10 32 1 0 0 0 0 11 21 1 0 0 0 0 11 32 1 0 0 0 0 12 18 2 0 0 0 0 12 42 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 24 2 0 0 0 0 15 28 1 0 0 0 0 16 24 1 0 0 0 0 16 29 1 0 0 0 0 17 23 2 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 0 0 0 0 19 35 2 0 0 0 0 20 36 2 0 0 0 0 21 37 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 22 34 2 0 0 0 0 23 40 1 0 0 0 0 24 41 1 0 0 0 0 25 27 1 6 0 0 0 25 38 1 0 0 0 0 26 33 1 0 0 0 0 26 39 2 0 0 0 0 27 9 1 6 0 0 0 27 42 1 0 0 0 0 27 43 1 0 0 0 0 34 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	850.83
Volume:	601.558
LogP:	3.455
LogD:	1.595
LogS:	-3.237
# Rotatable Bonds:	12
TPSA:	161.85
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.545
Fsp3:	0.37
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.186
MDCK Permeability:	1.7197093256982043e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.749
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	96.54279327392578%
Volume Distribution (VD):	1.279
Pgp-substrate:	4.9616379737854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.586
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.841

ADMET: Excretion

Clearance (CL):	1.002
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.372
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC470746

Natural Product ID:	NPC470746
*Common Name:**	19-Hydroxypsammaplysin E
IUPAC Name:	(4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[(2,5-dioxocyclopent-3-en-1-ylidene)methylamino]-1-hydroxyethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:	19-Hydroxypsammaplysin E
Standard InCHIKey:	ALQMQVUOKZVSGT-SLCPUWTHSA-N
Standard InCHI:	InChI=1S/C27H25Br4N3O9/c1-40-23-17(30)9-27(42-12-18(23)31)25(38)22(34-43-27)26(39)33-5-2-6-41-24-15(28)7-13(8-16(24)29)21(37)11-32-10-14-19(35)3-4-20(14)36/h3-4,7-8,10,12,21,25,32,37-38H,2,5-6,9,11H2,1H3,(H,33,39)/t21?,25-,27-/m0/s1
SMILES:	COC1=C(Br)C[C@]2(OC=C1Br)ON=C([C@@H]2O)C(=O)NCCCOc1c(Br)cc(cc1Br)C(CNC=C1C(=O)C=CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208225
PubChem CID:	71459809
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO32476	aplysinella strongylata	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23215158]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6400.0	nM	PMID[488850]

☑ 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 NPC470746 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	273
0.1-0.2	1644
0.2-0.3	8463
0.3-0.4	10015
0.4-0.5	13825
0.5-0.6	8200
0.6-0.7	245
0.7-0.8	9
0.8-0.85	11
0.85-0.9	4
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471336
0.962	High Similarity	NPC123140
0.9348	High Similarity	NPC475843
0.933	High Similarity	NPC471335
0.9293	High Similarity	NPC471338
0.9293	High Similarity	NPC474678
0.9101	High Similarity	NPC471337
0.8969	High Similarity	NPC471339
0.8967	High Similarity	NPC8093
0.8967	High Similarity	NPC121571
0.837	Intermediate Similarity	NPC477255
0.8272	Intermediate Similarity	NPC77435
0.8272	Intermediate Similarity	NPC259071
0.8168	Intermediate Similarity	NPC477254
0.8163	Intermediate Similarity	NPC202866
0.8112	Intermediate Similarity	NPC227953
0.7857	Intermediate Similarity	NPC174607
0.7817	Intermediate Similarity	NPC147847
0.7473	Intermediate Similarity	NPC469711
0.7354	Intermediate Similarity	NPC156311
0.71	Intermediate Similarity	NPC143450
0.7083	Intermediate Similarity	NPC233926
0.7053	Intermediate Similarity	NPC258222
0.7016	Intermediate Similarity	NPC47672
0.7011	Intermediate Similarity	NPC474673
0.6971	Remote Similarity	NPC248822
0.6911	Remote Similarity	NPC76412
0.6895	Remote Similarity	NPC71629
0.6882	Remote Similarity	NPC128877
0.6875	Remote Similarity	NPC109968
0.6869	Remote Similarity	NPC473450
0.6862	Remote Similarity	NPC308571
0.6827	Remote Similarity	NPC475658
0.6827	Remote Similarity	NPC473892
0.6806	Remote Similarity	NPC296085
0.6794	Remote Similarity	NPC82741
0.6794	Remote Similarity	NPC473409
0.6794	Remote Similarity	NPC141405
0.6737	Remote Similarity	NPC78530
0.6714	Remote Similarity	NPC246591
0.6699	Remote Similarity	NPC49172
0.6683	Remote Similarity	NPC471568
0.6683	Remote Similarity	NPC473693
0.6682	Remote Similarity	NPC214368
0.6667	Remote Similarity	NPC471591
0.6651	Remote Similarity	NPC469731
0.6649	Remote Similarity	NPC135349
0.6636	Remote Similarity	NPC469721
0.6636	Remote Similarity	NPC80514
0.6633	Remote Similarity	NPC235033
0.6633	Remote Similarity	NPC73132
0.6633	Remote Similarity	NPC471235
0.6632	Remote Similarity	NPC474128
0.6631	Remote Similarity	NPC470471
0.662	Remote Similarity	NPC102245
0.6617	Remote Similarity	NPC469479
0.6601	Remote Similarity	NPC196091
0.6589	Remote Similarity	NPC65714
0.6588	Remote Similarity	NPC96275
0.6578	Remote Similarity	NPC326027
0.6571	Remote Similarity	NPC299806
0.6562	Remote Similarity	NPC470472
0.6562	Remote Similarity	NPC326333
0.6561	Remote Similarity	NPC470470
0.6559	Remote Similarity	NPC97870
0.6559	Remote Similarity	NPC307123
0.6559	Remote Similarity	NPC247018
0.6552	Remote Similarity	NPC186617
0.6542	Remote Similarity	NPC64066
0.6526	Remote Similarity	NPC283207
0.6507	Remote Similarity	NPC475396
0.6498	Remote Similarity	NPC471592
0.6476	Remote Similarity	NPC301941
0.6476	Remote Similarity	NPC214188
0.6476	Remote Similarity	NPC74618
0.6471	Remote Similarity	NPC469505
0.6442	Remote Similarity	NPC469979
0.6429	Remote Similarity	NPC324081
0.6411	Remote Similarity	NPC110454
0.6411	Remote Similarity	NPC298981
0.6411	Remote Similarity	NPC207819
0.6411	Remote Similarity	NPC126128
0.6411	Remote Similarity	NPC473462
0.6404	Remote Similarity	NPC158900
0.6393	Remote Similarity	NPC477550
0.6393	Remote Similarity	NPC323662
0.6393	Remote Similarity	NPC477552
0.6381	Remote Similarity	NPC290534
0.6373	Remote Similarity	NPC204546
0.6372	Remote Similarity	NPC230539
0.6364	Remote Similarity	NPC123859
0.6364	Remote Similarity	NPC226001
0.6359	Remote Similarity	NPC272463
0.6355	Remote Similarity	NPC144823
0.6355	Remote Similarity	NPC80337
0.6338	Remote Similarity	NPC315542
0.6335	Remote Similarity	NPC477551
0.6335	Remote Similarity	NPC242728
0.6333	Remote Similarity	NPC475421
0.6324	Remote Similarity	NPC110131
0.6321	Remote Similarity	NPC470112
0.6321	Remote Similarity	NPC470903
0.6321	Remote Similarity	NPC167763
0.6316	Remote Similarity	NPC225130
0.6308	Remote Similarity	NPC276120
0.6302	Remote Similarity	NPC213471
0.63	Remote Similarity	NPC470710
0.63	Remote Similarity	NPC123011
0.63	Remote Similarity	NPC197125
0.63	Remote Similarity	NPC256689
0.6293	Remote Similarity	NPC254700
0.6284	Remote Similarity	NPC328763
0.6273	Remote Similarity	NPC144314
0.6272	Remote Similarity	NPC92235
0.6268	Remote Similarity	NPC471165
0.6263	Remote Similarity	NPC20755
0.6262	Remote Similarity	NPC209463
0.6261	Remote Similarity	NPC476661
0.6256	Remote Similarity	NPC476194
0.6256	Remote Similarity	NPC471203
0.6244	Remote Similarity	NPC50548
0.6244	Remote Similarity	NPC472923
0.6238	Remote Similarity	NPC56635
0.6237	Remote Similarity	NPC320242
0.6234	Remote Similarity	NPC67658
0.6233	Remote Similarity	NPC476662
0.623	Remote Similarity	NPC470441
0.6227	Remote Similarity	NPC149962
0.6211	Remote Similarity	NPC474753
0.6205	Remote Similarity	NPC311357
0.6199	Remote Similarity	NPC281629
0.6193	Remote Similarity	NPC477526
0.6186	Remote Similarity	NPC138083
0.6186	Remote Similarity	NPC40321
0.6182	Remote Similarity	NPC184933
0.6182	Remote Similarity	NPC59827
0.6178	Remote Similarity	NPC132308
0.6178	Remote Similarity	NPC169766
0.6175	Remote Similarity	NPC124626
0.6172	Remote Similarity	NPC328494
0.6172	Remote Similarity	NPC89831
0.6166	Remote Similarity	NPC473055
0.6166	Remote Similarity	NPC473052
0.6165	Remote Similarity	NPC63931
0.6158	Remote Similarity	NPC475735
0.6158	Remote Similarity	NPC473724
0.6157	Remote Similarity	NPC14390
0.615	Remote Similarity	NPC14339
0.6146	Remote Similarity	NPC303993
0.6144	Remote Similarity	NPC175150
0.6144	Remote Similarity	NPC243633
0.6143	Remote Similarity	NPC248670
0.6134	Remote Similarity	NPC322526
0.6126	Remote Similarity	NPC470392
0.6116	Remote Similarity	NPC471031
0.6116	Remote Similarity	NPC469689
0.6114	Remote Similarity	NPC477160
0.6114	Remote Similarity	NPC196708
0.6111	Remote Similarity	NPC235194
0.6108	Remote Similarity	NPC471073
0.6108	Remote Similarity	NPC270811
0.6106	Remote Similarity	NPC473502
0.6105	Remote Similarity	NPC474091
0.6105	Remote Similarity	NPC474087
0.6103	Remote Similarity	NPC475615
0.6101	Remote Similarity	NPC471395
0.6099	Remote Similarity	NPC477527
0.6089	Remote Similarity	NPC156055
0.6089	Remote Similarity	NPC39431
0.6085	Remote Similarity	NPC477115
0.608	Remote Similarity	NPC313414
0.6079	Remote Similarity	NPC81845
0.6075	Remote Similarity	NPC32064
0.6073	Remote Similarity	NPC29531
0.6073	Remote Similarity	NPC11449
0.6071	Remote Similarity	NPC470709
0.6066	Remote Similarity	NPC273755
0.6064	Remote Similarity	NPC141739
0.6064	Remote Similarity	NPC136112
0.6059	Remote Similarity	NPC476268
0.6059	Remote Similarity	NPC244509
0.6058	Remote Similarity	NPC71205
0.6055	Remote Similarity	NPC94862
0.6055	Remote Similarity	NPC34780
0.6051	Remote Similarity	NPC471201
0.6051	Remote Similarity	NPC197045
0.605	Remote Similarity	NPC132771
0.6049	Remote Similarity	NPC319320
0.6049	Remote Similarity	NPC287757
0.6048	Remote Similarity	NPC46009
0.6047	Remote Similarity	NPC28368
0.6045	Remote Similarity	NPC473407
0.6045	Remote Similarity	NPC473378
0.6043	Remote Similarity	NPC293347
0.6041	Remote Similarity	NPC314702
0.6038	Remote Similarity	NPC26108
0.6038	Remote Similarity	NPC164608
0.603	Remote Similarity	NPC119569
0.6027	Remote Similarity	NPC470951
0.6026	Remote Similarity	NPC257266

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 NPC470746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	598
0.2-0.3	1472
0.3-0.4	2525
0.4-0.5	3124
0.5-0.6	1203
0.6-0.7	66
0.7-0.8	0
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
0.6748	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3153	Approved
0.6619	Remote Similarity	NPD3154	Approved
0.6614	Remote Similarity	NPD2240	Approved
0.6614	Remote Similarity	NPD2239	Approved
0.6559	Remote Similarity	NPD1423	Approved
0.6513	Remote Similarity	NPD3536	Discontinued
0.6465	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3180	Approved
0.6452	Remote Similarity	NPD3179	Approved
0.6439	Remote Similarity	NPD7608	Discontinued
0.6429	Remote Similarity	NPD4662	Approved
0.6429	Remote Similarity	NPD4661	Approved
0.6425	Remote Similarity	NPD6863	Phase 2
0.6425	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8059	Phase 3
0.6383	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4466	Phase 1
0.6355	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7038	Approved
0.6351	Remote Similarity	NPD7039	Approved
0.6332	Remote Similarity	NPD3687	Approved
0.6332	Remote Similarity	NPD3686	Approved
0.6324	Remote Similarity	NPD8031	Discontinued
0.6305	Remote Similarity	NPD7318	Phase 3
0.63	Remote Similarity	NPD2649	Approved
0.63	Remote Similarity	NPD2651	Approved
0.629	Remote Similarity	NPD7811	Phase 3
0.629	Remote Similarity	NPD7810	Phase 3
0.6283	Remote Similarity	NPD3052	Approved
0.6283	Remote Similarity	NPD3054	Approved
0.6281	Remote Similarity	NPD7131	Phase 3
0.6269	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7256	Discontinued
0.6244	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD1819	Approved
0.6237	Remote Similarity	NPD1817	Approved
0.6237	Remote Similarity	NPD1818	Approved
0.6237	Remote Similarity	NPD1820	Approved
0.6232	Remote Similarity	NPD7485	Phase 3
0.6232	Remote Similarity	NPD7484	Phase 3
0.6221	Remote Similarity	NPD4258	Approved
0.6221	Remote Similarity	NPD4259	Approved
0.6207	Remote Similarity	NPD7317	Phase 3
0.6197	Remote Similarity	NPD1298	Discontinued
0.619	Remote Similarity	NPD3165	Approved
0.619	Remote Similarity	NPD3167	Approved
0.619	Remote Similarity	NPD3164	Approved
0.619	Remote Similarity	NPD3166	Approved
0.6181	Remote Similarity	NPD3985	Discontinued
0.6176	Remote Similarity	NPD7972	Discontinued
0.6167	Remote Similarity	NPD7584	Approved
0.6161	Remote Similarity	NPD2163	Approved
0.6161	Remote Similarity	NPD7476	Discontinued
0.6158	Remote Similarity	NPD6072	Discontinued
0.6158	Remote Similarity	NPD6677	Suspended
0.6147	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7565	Approved
0.6135	Remote Similarity	NPD6315	Phase 2
0.6111	Remote Similarity	NPD2677	Approved
0.6106	Remote Similarity	NPD4666	Phase 3
0.6105	Remote Similarity	NPD9718	Approved
0.6103	Remote Similarity	NPD1725	Approved
0.61	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5773	Approved
0.6098	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5772	Approved
0.6095	Remote Similarity	NPD2215	Approved
0.6095	Remote Similarity	NPD2216	Approved
0.6095	Remote Similarity	NPD2388	Discontinued
0.6091	Remote Similarity	NPD4162	Approved
0.6078	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.607	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.607	Remote Similarity	NPD2186	Approved
0.6064	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1794	Approved
0.6058	Remote Similarity	NPD5709	Phase 3
0.6049	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3162	Approved
0.6042	Remote Similarity	NPD3163	Approved
0.604	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD5557	Phase 1
0.6026	Remote Similarity	NPD7583	Approved
0.602	Remote Similarity	NPD3157	Approved
0.602	Remote Similarity	NPD6419	Discontinued
0.602	Remote Similarity	NPD3158	Phase 1
0.6019	Remote Similarity	NPD2978	Approved
0.6019	Remote Similarity	NPD2977	Approved
0.601	Remote Similarity	NPD3060	Approved
0.601	Remote Similarity	NPD2460	Phase 3
0.601	Remote Similarity	NPD2458	Approved
0.601	Remote Similarity	NPD2459	Approved
0.6009	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6620	Discovery
0.6	Remote Similarity	NPD7585	Approved
0.5991	Remote Similarity	NPD6823	Phase 2
0.599	Remote Similarity	NPD2183	Approved
0.599	Remote Similarity	NPD2184	Approved
0.599	Remote Similarity	NPD2296	Approved
0.5982	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5356	Approved
0.5971	Remote Similarity	NPD5355	Approved
0.597	Remote Similarity	NPD1774	Approved
0.5964	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3366	Approved
0.5959	Remote Similarity	NPD5745	Approved
0.5955	Remote Similarity	NPD4157	Discontinued
0.5952	Remote Similarity	NPD2904	Discontinued
0.5945	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD644	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5137	Approved
0.5941	Remote Similarity	NPD2874	Phase 2
0.5939	Remote Similarity	NPD7891	Discontinued
0.5938	Remote Similarity	NPD5163	Phase 2
0.5935	Remote Similarity	NPD3909	Discontinued
0.5935	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD4210	Discontinued
0.5928	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD2250	Discontinued
0.5915	Remote Similarity	NPD7930	Approved
0.5913	Remote Similarity	NPD7999	Approved
0.5911	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD52	Approved
0.5911	Remote Similarity	NPD7526	Approved
0.5909	Remote Similarity	NPD7978	Discontinued
0.5909	Remote Similarity	NPD8469	Approved
0.5907	Remote Similarity	NPD6042	Phase 2
0.5907	Remote Similarity	NPD42	Phase 2
0.5905	Remote Similarity	NPD6862	Phase 2
0.5903	Remote Similarity	NPD6519	Phase 2
0.5903	Remote Similarity	NPD5457	Discontinued
0.5903	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7827	Phase 1
0.589	Remote Similarity	NPD6853	Approved
0.589	Remote Similarity	NPD6851	Approved
0.5888	Remote Similarity	NPD5605	Phase 2
0.5887	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3490	Discontinued
0.5879	Remote Similarity	NPD6681	Discovery
0.5879	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD7153	Discontinued
0.5874	Remote Similarity	NPD7296	Approved
0.5874	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD3263	Phase 3
0.5865	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3146	Approved
0.5862	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.5861	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD2161	Phase 2
0.5857	Remote Similarity	NPD1307	Phase 2
0.5857	Remote Similarity	NPD1309	Phase 2
0.5855	Remote Similarity	NPD7801	Approved
0.5855	Remote Similarity	NPD5746	Approved
0.5855	Remote Similarity	NPD3136	Phase 2
0.5854	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD3823	Discontinued
0.5853	Remote Similarity	NPD6297	Approved
0.5852	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD8162	Phase 2
0.585	Remote Similarity	NPD5062	Approved
0.585	Remote Similarity	NPD5061	Approved
0.585	Remote Similarity	NPD4237	Approved
0.585	Remote Similarity	NPD4236	Phase 3
0.5849	Remote Similarity	NPD2247	Approved
0.5849	Remote Similarity	NPD2249	Approved
0.5845	Remote Similarity	NPD6386	Approved
0.5845	Remote Similarity	NPD6385	Approved
0.5842	Remote Similarity	NPD5295	Discontinued
0.5842	Remote Similarity	NPD3122	Phase 3
0.5841	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD3556	Approved
0.5837	Remote Similarity	NPD3558	Approved
0.5837	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD3557	Approved
0.5837	Remote Similarity	NPD3560	Approved
0.5833	Remote Similarity	NPD7613	Discontinued
0.5833	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD3656	Approved
0.5826	Remote Similarity	NPD3802	Phase 3
0.5818	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD6844	Discontinued
0.5813	Remote Similarity	NPD6087	Phase 1
0.5813	Remote Similarity	NPD4357	Discontinued
0.5812	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD7693	Approved
0.581	Remote Similarity	NPD8398	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