NPASS Compound

Structure

NPC469711 OpenBabel07101718192D 21 21 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 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 0.8660 1.5000 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 -1.7321 -0.0000 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 3.4641 -1.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 21 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 17 3 0 0 0 0 8 11 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.95
Volume:	306.957
LogP:	1.559
LogD:	0.601
LogS:	-2.982
# Rotatable Bonds:	8
TPSA:	108.37
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	3.263
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.421
MDCK Permeability:	2.298260005773045e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.415
Plasma Protein Binding (PPB):	74.00572967529297%
Volume Distribution (VD):	0.647
Pgp-substrate:	29.90190315246582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.426
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	1.794
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.564
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.476
Carcinogencity:	0.109
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC469711

Natural Product ID:	NPC469711
*Common Name:**	Hydroxyceratinamine
IUPAC Name:	N-[3-[4-(2-amino-1-hydroxyethyl)-2,6-dibromophenoxy]propyl]-1-cyanoformamide
Synonyms:	7-Hydroxyceratinamine
Standard InCHIKey:	BKBCHPBOYFBMRI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H15Br2N3O3/c14-9-4-8(11(19)6-16)5-10(15)13(9)21-3-1-2-18-12(20)7-17/h4-5,11,19H,1-3,6,16H2,(H,18,20)
SMILES:	NCC(c1cc(Br)c(c(c1)Br)OCCCNC(=O)C#N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162273
PubChem CID:	10693462
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
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425148]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473442]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964644]
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24758268]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]
NPT2477	Cell Line	NUGC-3	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	>	70000.0	nM	PMID[475783]

☑ 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 NPC469711 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	225
0.1-0.2	2380
0.2-0.3	11935
0.3-0.4	7349
0.4-0.5	12766
0.5-0.6	7598
0.6-0.7	377
0.7-0.8	57
0.8-0.85	6
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.922	High Similarity	NPC128877
0.9014	High Similarity	NPC474673
0.8767	High Similarity	NPC308571
0.8169	Intermediate Similarity	NPC272463
0.8035	Intermediate Similarity	NPC474678
0.8035	Intermediate Similarity	NPC471338
0.7989	Intermediate Similarity	NPC475843
0.7986	Intermediate Similarity	NPC110131
0.7962	Intermediate Similarity	NPC47672
0.7949	Intermediate Similarity	NPC76412
0.7935	Intermediate Similarity	NPC296085
0.7935	Intermediate Similarity	NPC71629
0.7925	Intermediate Similarity	NPC233926
0.7857	Intermediate Similarity	NPC78530
0.7812	Intermediate Similarity	NPC156311
0.7791	Intermediate Similarity	NPC77435
0.7791	Intermediate Similarity	NPC259071
0.777	Intermediate Similarity	NPC474087
0.7765	Intermediate Similarity	NPC471337
0.7748	Intermediate Similarity	NPC470471
0.7688	Intermediate Similarity	NPC121571
0.7688	Intermediate Similarity	NPC8093
0.7665	Intermediate Similarity	NPC477255
0.7647	Intermediate Similarity	NPC470470
0.7628	Intermediate Similarity	NPC135349
0.7627	Intermediate Similarity	NPC227953
0.7486	Intermediate Similarity	NPC202866
0.7473	Intermediate Similarity	NPC471336
0.7473	Intermediate Similarity	NPC470746
0.7471	Intermediate Similarity	NPC477254
0.7453	Intermediate Similarity	NPC258222
0.7405	Intermediate Similarity	NPC470472
0.7394	Intermediate Similarity	NPC115803
0.7345	Intermediate Similarity	NPC174607
0.7303	Intermediate Similarity	NPC147847
0.7244	Intermediate Similarity	NPC470249
0.7244	Intermediate Similarity	NPC470248
0.7239	Intermediate Similarity	NPC109968
0.7202	Intermediate Similarity	NPC471335
0.719	Intermediate Similarity	NPC135173
0.7189	Intermediate Similarity	NPC123140
0.7179	Intermediate Similarity	NPC235633
0.7152	Intermediate Similarity	NPC320242
0.7097	Intermediate Similarity	NPC307123
0.7097	Intermediate Similarity	NPC247018
0.7097	Intermediate Similarity	NPC97870
0.7088	Intermediate Similarity	NPC64066
0.7083	Intermediate Similarity	NPC59387
0.7033	Intermediate Similarity	NPC248822
0.6986	Remote Similarity	NPC213
0.6986	Remote Similarity	NPC10286
0.6957	Remote Similarity	NPC204546
0.6957	Remote Similarity	NPC474128
0.6954	Remote Similarity	NPC116562
0.6937	Remote Similarity	NPC40321
0.6928	Remote Similarity	NPC141739
0.6928	Remote Similarity	NPC136112
0.6927	Remote Similarity	NPC471339
0.6915	Remote Similarity	NPC473450
0.6832	Remote Similarity	NPC470250
0.6815	Remote Similarity	NPC11449
0.6806	Remote Similarity	NPC145638
0.6806	Remote Similarity	NPC290566
0.6797	Remote Similarity	NPC328267
0.679	Remote Similarity	NPC470709
0.6776	Remote Similarity	NPC80337
0.6776	Remote Similarity	NPC475658
0.6776	Remote Similarity	NPC473892
0.6774	Remote Similarity	NPC218323
0.6753	Remote Similarity	NPC95733
0.6753	Remote Similarity	NPC62101
0.6739	Remote Similarity	NPC141405
0.6739	Remote Similarity	NPC82741
0.6739	Remote Similarity	NPC473409
0.6739	Remote Similarity	NPC246591
0.6735	Remote Similarity	NPC26524
0.671	Remote Similarity	NPC29477
0.6709	Remote Similarity	NPC473724
0.6709	Remote Similarity	NPC326599
0.6709	Remote Similarity	NPC329595
0.6707	Remote Similarity	NPC20755
0.6703	Remote Similarity	NPC230539
0.6689	Remote Similarity	NPC235250
0.6685	Remote Similarity	NPC471591
0.6667	Remote Similarity	NPC213471
0.6647	Remote Similarity	NPC235033
0.6647	Remote Similarity	NPC471235
0.6647	Remote Similarity	NPC73132
0.6645	Remote Similarity	NPC180207
0.6643	Remote Similarity	NPC8302
0.6631	Remote Similarity	NPC102245
0.663	Remote Similarity	NPC49172
0.6625	Remote Similarity	NPC243404
0.6624	Remote Similarity	NPC159987
0.6624	Remote Similarity	NPC122359
0.6624	Remote Similarity	NPC78061
0.6611	Remote Similarity	NPC143450
0.6604	Remote Similarity	NPC475735
0.6601	Remote Similarity	NPC318357
0.6582	Remote Similarity	NPC283079
0.6581	Remote Similarity	NPC211218
0.6581	Remote Similarity	NPC105999
0.6566	Remote Similarity	NPC79076
0.6564	Remote Similarity	NPC197045
0.6561	Remote Similarity	NPC469721
0.6561	Remote Similarity	NPC80514
0.6538	Remote Similarity	NPC213414
0.6534	Remote Similarity	NPC469479
0.6528	Remote Similarity	NPC42383
0.6519	Remote Similarity	NPC280736
0.6507	Remote Similarity	NPC97811
0.6505	Remote Similarity	NPC96275
0.6481	Remote Similarity	NPC303993
0.6474	Remote Similarity	NPC473572
0.6474	Remote Similarity	NPC474169
0.6463	Remote Similarity	NPC231163
0.6463	Remote Similarity	NPC54543
0.6463	Remote Similarity	NPC318591
0.646	Remote Similarity	NPC474753
0.646	Remote Similarity	NPC158078
0.6456	Remote Similarity	NPC236347
0.6456	Remote Similarity	NPC323775
0.6447	Remote Similarity	NPC137096
0.6438	Remote Similarity	NPC251306
0.6438	Remote Similarity	NPC195902
0.6438	Remote Similarity	NPC262641
0.6438	Remote Similarity	NPC474091
0.6436	Remote Similarity	NPC283207
0.6429	Remote Similarity	NPC321133
0.6429	Remote Similarity	NPC263835
0.6419	Remote Similarity	NPC473358
0.6416	Remote Similarity	NPC270811
0.6416	Remote Similarity	NPC471073
0.6415	Remote Similarity	NPC474147
0.6415	Remote Similarity	NPC473708
0.6412	Remote Similarity	NPC324081
0.641	Remote Similarity	NPC229213
0.641	Remote Similarity	NPC298486
0.641	Remote Similarity	NPC296202
0.6407	Remote Similarity	NPC470247
0.6406	Remote Similarity	NPC469731
0.6404	Remote Similarity	NPC293871
0.6404	Remote Similarity	NPC124433
0.6402	Remote Similarity	NPC307682
0.64	Remote Similarity	NPC160931
0.64	Remote Similarity	NPC37205
0.64	Remote Similarity	NPC301735
0.6398	Remote Similarity	NPC70485
0.6391	Remote Similarity	NPC313414
0.6391	Remote Similarity	NPC17760
0.6389	Remote Similarity	NPC305205
0.6369	Remote Similarity	NPC469505
0.6369	Remote Similarity	NPC13020
0.6369	Remote Similarity	NPC140359
0.6358	Remote Similarity	NPC470392
0.6352	Remote Similarity	NPC322366
0.6352	Remote Similarity	NPC43706
0.6348	Remote Similarity	NPC254700
0.6346	Remote Similarity	NPC7830
0.6345	Remote Similarity	NPC108875
0.6345	Remote Similarity	NPC38079
0.6339	Remote Similarity	NPC469979
0.6339	Remote Similarity	NPC226001
0.6335	Remote Similarity	NPC478071
0.6335	Remote Similarity	NPC99280
0.6329	Remote Similarity	NPC236265
0.6327	Remote Similarity	NPC186469
0.6325	Remote Similarity	NPC282087
0.6325	Remote Similarity	NPC318984
0.6325	Remote Similarity	NPC231572
0.6325	Remote Similarity	NPC317741
0.6325	Remote Similarity	NPC328137
0.6325	Remote Similarity	NPC241086
0.6325	Remote Similarity	NPC197239
0.6325	Remote Similarity	NPC326860
0.6325	Remote Similarity	NPC318028
0.6325	Remote Similarity	NPC259800
0.6323	Remote Similarity	NPC118522
0.6323	Remote Similarity	NPC169207
0.6323	Remote Similarity	NPC115627
0.6319	Remote Similarity	NPC327226
0.6309	Remote Similarity	NPC25067
0.6309	Remote Similarity	NPC88868
0.6309	Remote Similarity	NPC231251
0.6304	Remote Similarity	NPC298981
0.6304	Remote Similarity	NPC473462
0.6304	Remote Similarity	NPC110454
0.6304	Remote Similarity	NPC207819
0.6304	Remote Similarity	NPC126128
0.6301	Remote Similarity	NPC152947
0.6301	Remote Similarity	NPC470393
0.6296	Remote Similarity	NPC226493
0.6296	Remote Similarity	NPC160081
0.6294	Remote Similarity	NPC189908
0.6291	Remote Similarity	NPC471488
0.6287	Remote Similarity	NPC189724
0.6287	Remote Similarity	NPC212850
0.6287	Remote Similarity	NPC83289
0.6284	Remote Similarity	NPC471495
0.6272	Remote Similarity	NPC184632

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 NPC469711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	736
0.2-0.3	1570
0.3-0.4	2500
0.4-0.5	2677
0.5-0.6	1223
0.6-0.7	278
0.7-0.8	10
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
0.7403	Intermediate Similarity	NPD3054	Approved
0.7403	Intermediate Similarity	NPD3052	Approved
0.719	Intermediate Similarity	NPD3180	Approved
0.719	Intermediate Similarity	NPD3179	Approved
0.719	Intermediate Similarity	NPD9718	Approved
0.7152	Intermediate Similarity	NPD1819	Approved
0.7152	Intermediate Similarity	NPD1817	Approved
0.7152	Intermediate Similarity	NPD1818	Approved
0.7152	Intermediate Similarity	NPD1820	Approved
0.7143	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3536	Discontinued
0.7097	Intermediate Similarity	NPD1423	Approved
0.7007	Intermediate Similarity	NPD16	Approved
0.7007	Intermediate Similarity	NPD856	Approved
0.6988	Remote Similarity	NPD3687	Approved
0.6988	Remote Similarity	NPD3686	Approved
0.6987	Remote Similarity	NPD2245	Discovery
0.6968	Remote Similarity	NPD3166	Approved
0.6968	Remote Similarity	NPD3165	Approved
0.6968	Remote Similarity	NPD5163	Phase 2
0.6968	Remote Similarity	NPD3167	Approved
0.6968	Remote Similarity	NPD3164	Approved
0.6937	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1794	Approved
0.6909	Remote Similarity	NPD3158	Phase 1
0.6909	Remote Similarity	NPD3157	Approved
0.6892	Remote Similarity	NPD317	Approved
0.6892	Remote Similarity	NPD318	Approved
0.686	Remote Similarity	NPD8031	Discontinued
0.6842	Remote Similarity	NPD2231	Phase 2
0.6842	Remote Similarity	NPD2235	Phase 2
0.6832	Remote Similarity	NPD2239	Approved
0.6832	Remote Similarity	NPD2240	Approved
0.681	Remote Similarity	NPD4162	Approved
0.681	Remote Similarity	NPD3060	Approved
0.6807	Remote Similarity	NPD3985	Discontinued
0.6806	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2429	Approved
0.6797	Remote Similarity	NPD2428	Approved
0.6755	Remote Similarity	NPD2554	Approved
0.6755	Remote Similarity	NPD2556	Approved
0.6732	Remote Similarity	NPD2561	Approved
0.6732	Remote Similarity	NPD2562	Approved
0.6727	Remote Similarity	NPD2677	Approved
0.6723	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6419	Discontinued
0.6704	Remote Similarity	NPD42	Phase 2
0.6704	Remote Similarity	NPD6042	Phase 2
0.6667	Remote Similarity	NPD558	Phase 2
0.6667	Remote Similarity	NPD5745	Approved
0.6667	Remote Similarity	NPD3163	Approved
0.6667	Remote Similarity	NPD3162	Approved
0.6667	Remote Similarity	NPD2183	Approved
0.6667	Remote Similarity	NPD2184	Approved
0.6646	Remote Similarity	NPD6179	Discontinued
0.6631	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5709	Phase 3
0.6628	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7131	Phase 3
0.6625	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5061	Approved
0.6606	Remote Similarity	NPD5062	Approved
0.6606	Remote Similarity	NPD2458	Approved
0.6606	Remote Similarity	NPD2459	Approved
0.6606	Remote Similarity	NPD2460	Phase 3
0.6603	Remote Similarity	NPD1134	Approved
0.6603	Remote Similarity	NPD1131	Approved
0.6603	Remote Similarity	NPD1133	Approved
0.6603	Remote Similarity	NPD1135	Approved
0.6603	Remote Similarity	NPD1129	Approved
0.6603	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4666	Phase 3
0.6591	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5295	Discontinued
0.657	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3532	Approved
0.6562	Remote Similarity	NPD3530	Approved
0.6562	Remote Similarity	NPD6405	Approved
0.6562	Remote Similarity	NPD6407	Approved
0.6562	Remote Similarity	NPD3531	Approved
0.6548	Remote Similarity	NPD1774	Approved
0.6541	Remote Similarity	NPD5746	Approved
0.6538	Remote Similarity	NPD196	Phase 1
0.6527	Remote Similarity	NPD5160	Discontinued
0.6524	Remote Similarity	NPD1725	Approved
0.6513	Remote Similarity	NPD316	Approved
0.6509	Remote Similarity	NPD2874	Phase 2
0.6503	Remote Similarity	NPD1298	Discontinued
0.65	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6667	Approved
0.6488	Remote Similarity	NPD6666	Approved
0.6488	Remote Similarity	NPD3122	Phase 3
0.648	Remote Similarity	NPD2388	Discontinued
0.6471	Remote Similarity	NPD3049	Approved
0.6467	Remote Similarity	NPD595	Approved
0.6467	Remote Similarity	NPD593	Approved
0.6463	Remote Similarity	NPD2154	Approved
0.6463	Remote Similarity	NPD2156	Approved
0.6463	Remote Similarity	NPD2155	Approved
0.6461	Remote Similarity	NPD7485	Phase 3
0.6461	Remote Similarity	NPD7484	Phase 3
0.6456	Remote Similarity	NPD9619	Approved
0.6456	Remote Similarity	NPD9620	Approved
0.6456	Remote Similarity	NPD9621	Approved
0.6447	Remote Similarity	NPD9613	Approved
0.6447	Remote Similarity	NPD9615	Approved
0.6447	Remote Similarity	NPD9616	Approved
0.6437	Remote Similarity	NPD5355	Approved
0.6437	Remote Similarity	NPD5356	Approved
0.6433	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2667	Approved
0.6429	Remote Similarity	NPD2668	Approved
0.6416	Remote Similarity	NPD1009	Approved
0.6407	Remote Similarity	NPD4237	Approved
0.6407	Remote Similarity	NPD4236	Phase 3
0.64	Remote Similarity	NPD5773	Approved
0.64	Remote Similarity	NPD5772	Approved
0.6398	Remote Similarity	NPD601	Approved
0.6398	Remote Similarity	NPD1336	Approved
0.6398	Remote Similarity	NPD597	Approved
0.6398	Remote Similarity	NPD598	Approved
0.6395	Remote Similarity	NPD4210	Discontinued
0.6386	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2614	Approved
0.6375	Remote Similarity	NPD596	Approved
0.6375	Remote Similarity	NPD600	Approved
0.6374	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6582	Phase 2
0.6369	Remote Similarity	NPD6583	Phase 3
0.6369	Remote Similarity	NPD3685	Discontinued
0.6364	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3556	Approved
0.6364	Remote Similarity	NPD3557	Approved
0.6364	Remote Similarity	NPD3558	Approved
0.6364	Remote Similarity	NPD3560	Approved
0.6358	Remote Similarity	NPD840	Approved
0.6358	Remote Similarity	NPD839	Approved
0.6358	Remote Similarity	NPD829	Discontinued
0.6358	Remote Similarity	NPD1136	Approved
0.6358	Remote Similarity	NPD1132	Approved
0.6358	Remote Similarity	NPD1130	Approved
0.6354	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7212	Phase 2
0.6353	Remote Similarity	NPD7213	Phase 3
0.6352	Remote Similarity	NPD599	Approved
0.6352	Remote Similarity	NPD3691	Phase 2
0.6352	Remote Similarity	NPD859	Approved
0.6352	Remote Similarity	NPD602	Approved
0.6352	Remote Similarity	NPD3690	Phase 2
0.6352	Remote Similarity	NPD858	Approved
0.6347	Remote Similarity	NPD7153	Discontinued
0.6347	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2653	Approved
0.6341	Remote Similarity	NPD5314	Approved
0.6325	Remote Similarity	NPD1519	Approved
0.6325	Remote Similarity	NPD3156	Discontinued
0.6325	Remote Similarity	NPD1522	Approved
0.6325	Remote Similarity	NPD1538	Phase 1
0.6325	Remote Similarity	NPD1523	Approved
0.6325	Remote Similarity	NPD1537	Approved
0.6324	Remote Similarity	NPD7039	Approved
0.6324	Remote Similarity	NPD7038	Approved
0.6323	Remote Similarity	NPD9381	Approved
0.6323	Remote Similarity	NPD9384	Approved
0.6319	Remote Similarity	NPD3061	Approved
0.6319	Remote Similarity	NPD2238	Phase 2
0.6319	Remote Similarity	NPD3059	Approved
0.6319	Remote Similarity	NPD3062	Approved
0.6316	Remote Similarity	NPD4661	Approved
0.6316	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4662	Approved
0.6313	Remote Similarity	NPD2904	Discontinued
0.6307	Remote Similarity	NPD2977	Approved
0.6307	Remote Similarity	NPD2978	Approved
0.6303	Remote Similarity	NPD3554	Approved
0.6303	Remote Similarity	NPD3553	Approved
0.6303	Remote Similarity	NPD1521	Approved
0.6303	Remote Similarity	NPD3552	Approved
0.6303	Remote Similarity	NPD3555	Approved
0.6303	Remote Similarity	NPD1520	Approved
0.6303	Remote Similarity	NPD1536	Approved
0.6298	Remote Similarity	NPD2216	Approved
0.6298	Remote Similarity	NPD2215	Approved
0.6294	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD1307	Phase 2
0.6292	Remote Similarity	NPD1309	Phase 2
0.6286	Remote Similarity	NPD6072	Discontinued
0.6286	Remote Similarity	NPD6677	Suspended
0.6279	Remote Similarity	NPD7526	Approved
0.6279	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2675	Approved
0.6279	Remote Similarity	NPD52	Approved
0.6279	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2676	Approved
0.6279	Remote Similarity	NPD2186	Approved
0.6275	Remote Similarity	NPD3596	Phase 2
0.6265	Remote Similarity	NPD3152	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