NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	540.23
Volume:	545.43
LogP:	4.621
LogD:	3.777
LogS:	-5.431
# Rotatable Bonds:	5
TPSA:	102.96
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	5.879
Fsp3:	0.483
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.994
MDCK Permeability:	1.34E-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.437
Plasma Protein Binding (PPB):	97.40%
Volume Distribution (VD):	1.868
Pgp-substrate:	1.97%

ADMET: Metabolism

CYP1A2-inhibitor:	0.192
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.957
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.432
CYP2D6-substrate:	0.749
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	6.458
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.562
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.819
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.975
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC477556

Natural Product ID:	NPC477556
*Common Name:**	[(1R,4Z,8E,10Z,12S,15R,17S)-5,12-dimethyl-3-oxo-17-[(4R)-2-oxo-1,3-thiazolidin-4-yl]-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl] N-phenylcarbamate
IUPAC Name:	[(1R,4Z,8E,10Z,12S,15R,17S)-5,12-dimethyl-3-oxo-17-[(4R)-2-oxo-1,3-thiazolidin-4-yl]-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl] N-phenylcarbamate
Synonyms:
Standard InCHIKey:	AJLVAOHKVXQLIG-WOZHBFIZSA-N
Standard InCHI:	InChI=1S/C29H36N2O6S/c1-20-10-6-3-4-7-11-21(2)16-26(32)35-24-17-23(15-14-20)36-29(18-24,25-19-38-28(34)31-25)37-27(33)30-22-12-8-5-9-13-22/h3-6,8-10,12-13,16,20,23-25H,7,11,14-15,17-19H2,1-2H3,(H,30,33)(H,31,34)/b4-3+,10-6-,21-16-/t20-,23-,24-,25+,29+/m1/s1
SMILES:	C[C@H]/1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]3CSC(=O)N3)OC(=O)NC4=CC=CC=C4)OC(=O)/C=C(\CC/C=C/C=C1)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24853748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217296]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499319]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast	2003-JUN	PMID[18298079]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	20	%	PMID[18298079]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	130016957.8	nM	PMID[20684858]
NPT2	Others	Unspecified		Inhibition	<	50	%	PMID[18298079]

☑ 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 NPC477556 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	141
0.1-0.2	878
0.2-0.3	3657
0.3-0.4	14014
0.4-0.5	20641
0.5-0.6	3170
0.6-0.7	184
0.7-0.8	10
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
0.9197	High Similarity	NPC477557
0.7338	Intermediate Similarity	NPC477554
0.7333	Intermediate Similarity	NPC474969
0.7333	Intermediate Similarity	NPC476034
0.7286	Intermediate Similarity	NPC477553
0.7259	Intermediate Similarity	NPC250187
0.7234	Intermediate Similarity	NPC477555
0.7206	Intermediate Similarity	NPC287572
0.7206	Intermediate Similarity	NPC471636
0.7059	Intermediate Similarity	NPC135216
0.7059	Intermediate Similarity	NPC101106
0.7029	Intermediate Similarity	NPC474891
0.695	Remote Similarity	NPC475988
0.6879	Remote Similarity	NPC295444
0.6879	Remote Similarity	NPC268327
0.6879	Remote Similarity	NPC273215
0.6879	Remote Similarity	NPC279383
0.6857	Remote Similarity	NPC127578
0.6776	Remote Similarity	NPC101372
0.6667	Remote Similarity	NPC210415
0.6667	Remote Similarity	NPC181138
0.6667	Remote Similarity	NPC276993
0.6667	Remote Similarity	NPC21752
0.6667	Remote Similarity	NPC293255
0.6667	Remote Similarity	NPC298851
0.6642	Remote Similarity	NPC474873
0.659	Remote Similarity	NPC469462
0.657	Remote Similarity	NPC52059
0.657	Remote Similarity	NPC470069
0.6564	Remote Similarity	NPC31171
0.6564	Remote Similarity	NPC237240
0.6529	Remote Similarity	NPC243673
0.6529	Remote Similarity	NPC148468
0.6529	Remote Similarity	NPC97380
0.6529	Remote Similarity	NPC310403
0.6529	Remote Similarity	NPC263709
0.6529	Remote Similarity	NPC63210
0.6524	Remote Similarity	NPC173934
0.6503	Remote Similarity	NPC282578
0.6503	Remote Similarity	NPC316405
0.6491	Remote Similarity	NPC474058
0.649	Remote Similarity	NPC160493
0.6484	Remote Similarity	NPC291759
0.6483	Remote Similarity	NPC273814
0.6474	Remote Similarity	NPC314473
0.6456	Remote Similarity	NPC64897
0.6456	Remote Similarity	NPC90693
0.645	Remote Similarity	NPC161827
0.6446	Remote Similarity	NPC201692
0.6443	Remote Similarity	NPC310467
0.6429	Remote Similarity	NPC133591
0.6424	Remote Similarity	NPC472100
0.642	Remote Similarity	NPC111586
0.642	Remote Similarity	NPC108852
0.642	Remote Similarity	NPC261709
0.6402	Remote Similarity	NPC262216
0.6376	Remote Similarity	NPC169328
0.6374	Remote Similarity	NPC211525
0.6374	Remote Similarity	NPC153694
0.6364	Remote Similarity	NPC470824
0.6364	Remote Similarity	NPC325013
0.6358	Remote Similarity	NPC190663
0.6358	Remote Similarity	NPC477061
0.6358	Remote Similarity	NPC35510
0.6358	Remote Similarity	NPC45777
0.6358	Remote Similarity	NPC80150
0.6358	Remote Similarity	NPC253667
0.6333	Remote Similarity	NPC6974
0.6329	Remote Similarity	NPC246079
0.6316	Remote Similarity	NPC36836
0.6316	Remote Similarity	NPC63370
0.6304	Remote Similarity	NPC207033
0.6304	Remote Similarity	NPC38823
0.6303	Remote Similarity	NPC472103
0.6301	Remote Similarity	NPC320064
0.6287	Remote Similarity	NPC283783
0.6264	Remote Similarity	NPC475962
0.6258	Remote Similarity	NPC239770
0.6257	Remote Similarity	NPC477526
0.625	Remote Similarity	NPC314861
0.6243	Remote Similarity	NPC476194
0.6234	Remote Similarity	NPC476278
0.6228	Remote Similarity	NPC97282
0.6228	Remote Similarity	NPC478039
0.6225	Remote Similarity	NPC237420
0.622	Remote Similarity	NPC314113
0.6215	Remote Similarity	NPC470971
0.6211	Remote Similarity	NPC108847
0.619	Remote Similarity	NPC474995
0.6184	Remote Similarity	NPC14950
0.6168	Remote Similarity	NPC136951
0.6168	Remote Similarity	NPC161155
0.6168	Remote Similarity	NPC97004
0.6167	Remote Similarity	NPC95412
0.6154	Remote Similarity	NPC99043
0.6154	Remote Similarity	NPC218594
0.6145	Remote Similarity	NPC83241
0.6145	Remote Similarity	NPC473922
0.6144	Remote Similarity	NPC478015
0.6144	Remote Similarity	NPC476183
0.6144	Remote Similarity	NPC478014
0.6144	Remote Similarity	NPC478016
0.6141	Remote Similarity	NPC159963
0.6139	Remote Similarity	NPC472413
0.6131	Remote Similarity	NPC105717
0.6129	Remote Similarity	NPC472415
0.6127	Remote Similarity	NPC477156
0.6127	Remote Similarity	NPC477157
0.6122	Remote Similarity	NPC323007
0.6121	Remote Similarity	NPC469360
0.6114	Remote Similarity	NPC156348
0.6108	Remote Similarity	NPC190945
0.6107	Remote Similarity	NPC474984
0.6104	Remote Similarity	NPC476281
0.6104	Remote Similarity	NPC476184
0.6101	Remote Similarity	NPC477432
0.6098	Remote Similarity	NPC319645
0.6096	Remote Similarity	NPC14994
0.6095	Remote Similarity	NPC13470
0.6093	Remote Similarity	NPC147957
0.6084	Remote Similarity	NPC123761
0.6082	Remote Similarity	NPC314223
0.6082	Remote Similarity	NPC4108
0.6069	Remote Similarity	NPC114808
0.6069	Remote Similarity	NPC473297
0.6067	Remote Similarity	NPC278887
0.6061	Remote Similarity	NPC197921
0.6054	Remote Similarity	NPC469831
0.6051	Remote Similarity	NPC472414
0.6045	Remote Similarity	NPC139506
0.6045	Remote Similarity	NPC292143
0.6044	Remote Similarity	NPC264482
0.6044	Remote Similarity	NPC203202
0.6037	Remote Similarity	NPC287358
0.6024	Remote Similarity	NPC91953
0.6022	Remote Similarity	NPC469829
0.6022	Remote Similarity	NPC225381
0.6012	Remote Similarity	NPC314186
0.6012	Remote Similarity	NPC49565
0.6011	Remote Similarity	NPC186669
0.6	Remote Similarity	NPC25401
0.6	Remote Similarity	NPC69496
0.599	Remote Similarity	NPC184933
0.599	Remote Similarity	NPC59827
0.5989	Remote Similarity	NPC278272
0.5989	Remote Similarity	NPC120667
0.5988	Remote Similarity	NPC233910
0.5988	Remote Similarity	NPC472761
0.5988	Remote Similarity	NPC286551
0.5988	Remote Similarity	NPC245836
0.5987	Remote Similarity	NPC476241
0.5987	Remote Similarity	NPC476260
0.5987	Remote Similarity	NPC317758
0.5986	Remote Similarity	NPC114741
0.5986	Remote Similarity	NPC182549
0.5986	Remote Similarity	NPC184633
0.5976	Remote Similarity	NPC135121
0.5973	Remote Similarity	NPC470825
0.5966	Remote Similarity	NPC469461
0.596	Remote Similarity	NPC470550
0.5954	Remote Similarity	NPC470902
0.5952	Remote Similarity	NPC314287
0.5952	Remote Similarity	NPC478040
0.5949	Remote Similarity	NPC477248
0.5949	Remote Similarity	NPC476125
0.5949	Remote Similarity	NPC477249
0.5949	Remote Similarity	NPC476179
0.5941	Remote Similarity	NPC473541
0.5939	Remote Similarity	NPC77992
0.5938	Remote Similarity	NPC116057
0.5938	Remote Similarity	NPC213969
0.5938	Remote Similarity	NPC165726
0.5938	Remote Similarity	NPC71271
0.5936	Remote Similarity	NPC97584
0.5933	Remote Similarity	NPC477246
0.5933	Remote Similarity	NPC477245
0.5932	Remote Similarity	NPC477158
0.5932	Remote Similarity	NPC231862
0.5931	Remote Similarity	NPC113326
0.5931	Remote Similarity	NPC88267
0.5931	Remote Similarity	NPC194390
0.5931	Remote Similarity	NPC224610
0.5928	Remote Similarity	NPC316202
0.5928	Remote Similarity	NPC298821
0.5926	Remote Similarity	NPC246913
0.5926	Remote Similarity	NPC329731
0.5926	Remote Similarity	NPC469830
0.5926	Remote Similarity	NPC313466
0.5926	Remote Similarity	NPC4910
0.5922	Remote Similarity	NPC70172
0.5916	Remote Similarity	NPC28510
0.5914	Remote Similarity	NPC475345
0.5907	Remote Similarity	NPC476129
0.5907	Remote Similarity	NPC259791
0.5907	Remote Similarity	NPC476256
0.5907	Remote Similarity	NPC476205
0.5907	Remote Similarity	NPC476212
0.5907	Remote Similarity	NPC476257
0.5907	Remote Similarity	NPC476207
0.5907	Remote Similarity	NPC476206

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 NPC477556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	447
0.2-0.3	803
0.3-0.4	1602
0.4-0.5	4539
0.5-0.6	1589
0.6-0.7	66
0.7-0.8	1
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
0.7059	Intermediate Similarity	NPD4211	Phase 1
0.6709	Remote Similarity	NPD6865	Phase 2
0.6709	Remote Similarity	NPD6864	Phase 2
0.6687	Remote Similarity	NPD6378	Approved
0.6667	Remote Similarity	NPD6885	Approved
0.6667	Remote Similarity	NPD6886	Approved
0.66	Remote Similarity	NPD4480	Approved
0.6564	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6392	Approved
0.6474	Remote Similarity	NPD7036	Phase 3
0.6474	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7035	Approved
0.645	Remote Similarity	NPD2891	Approved
0.6429	Remote Similarity	NPD6391	Approved
0.6424	Remote Similarity	NPD4607	Approved
0.6424	Remote Similarity	NPD5770	Phase 3
0.641	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4513	Discontinued
0.64	Remote Similarity	NPD2034	Discontinued
0.64	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3352	Approved
0.638	Remote Similarity	NPD2923	Approved
0.638	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6913	Approved
0.6316	Remote Similarity	NPD6571	Approved
0.6316	Remote Similarity	NPD6570	Approved
0.631	Remote Similarity	NPD6390	Discontinued
0.6303	Remote Similarity	NPD2387	Approved
0.6265	Remote Similarity	NPD6185	Discontinued
0.6258	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5076	Approved
0.6257	Remote Similarity	NPD5077	Approved
0.625	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4557	Approved
0.6243	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8007	Approved
0.6229	Remote Similarity	NPD8008	Approved
0.6228	Remote Similarity	NPD4041	Approved
0.6221	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7600	Phase 2
0.6207	Remote Similarity	NPD7156	Discontinued
0.619	Remote Similarity	NPD6758	Approved
0.6188	Remote Similarity	NPD2112	Phase 2
0.617	Remote Similarity	NPD6659	Phase 2
0.6167	Remote Similarity	NPD7940	Phase 3
0.6164	Remote Similarity	NPD3720	Discontinued
0.6164	Remote Similarity	NPD4738	Phase 2
0.6164	Remote Similarity	NPD4274	Approved
0.6164	Remote Similarity	NPD4275	Approved
0.6154	Remote Similarity	NPD7775	Approved
0.6145	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3399	Approved
0.614	Remote Similarity	NPD4648	Approved
0.614	Remote Similarity	NPD4647	Approved
0.614	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4646	Approved
0.6118	Remote Similarity	NPD6093	Discontinued
0.6114	Remote Similarity	NPD7244	Discontinued
0.6108	Remote Similarity	NPD2435	Approved
0.6107	Remote Similarity	NPD23	Approved
0.6105	Remote Similarity	NPD1634	Approved
0.6105	Remote Similarity	NPD5811	Approved
0.6098	Remote Similarity	NPD1109	Approved
0.6098	Remote Similarity	NPD1110	Approved
0.6098	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6891	Phase 2
0.6095	Remote Similarity	NPD2013	Approved
0.6095	Remote Similarity	NPD2014	Approved
0.6095	Remote Similarity	NPD1340	Discontinued
0.6095	Remote Similarity	NPD2016	Approved
0.6085	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD4514	Approved
0.6057	Remote Similarity	NPD7599	Phase 2
0.6057	Remote Similarity	NPD3388	Phase 1
0.6057	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD9587	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5185	Approved
0.6049	Remote Similarity	NPD5182	Approved
0.6049	Remote Similarity	NPD5184	Approved
0.6047	Remote Similarity	NPD1633	Approved
0.6038	Remote Similarity	NPD4006	Discontinued
0.6037	Remote Similarity	NPD6852	Discontinued
0.6034	Remote Similarity	NPD7105	Phase 1
0.6033	Remote Similarity	NPD6878	Phase 2
0.6033	Remote Similarity	NPD6879	Phase 2
0.6026	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD864	Approved
0.6025	Remote Similarity	NPD865	Approved
0.6023	Remote Similarity	NPD5230	Approved
0.6023	Remote Similarity	NPD5229	Approved
0.6011	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD4587	Phase 3
0.6011	Remote Similarity	NPD3965	Phase 1
0.6	Remote Similarity	NPD2613	Approved
0.6	Remote Similarity	NPD1655	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5570	Discontinued
0.6	Remote Similarity	NPD3170	Approved
0.5988	Remote Similarity	NPD2573	Approved
0.5988	Remote Similarity	NPD3614	Approved
0.5988	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD3087	Approved
0.5988	Remote Similarity	NPD3616	Approved
0.5988	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD3088	Approved
0.5988	Remote Similarity	NPD4746	Phase 3
0.5988	Remote Similarity	NPD2566	Approved
0.5988	Remote Similarity	NPD2570	Approved
0.5988	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD3615	Approved
0.5988	Remote Similarity	NPD3089	Approved
0.5988	Remote Similarity	NPD4745	Approved
0.5988	Remote Similarity	NPD3090	Approved
0.5988	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD2574	Discontinued
0.5988	Remote Similarity	NPD2571	Approved
0.5977	Remote Similarity	NPD7822	Phase 1
0.5976	Remote Similarity	NPD6622	Phase 1
0.5976	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD7247	Discontinued
0.5974	Remote Similarity	NPD3535	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD2212	Approved
0.5974	Remote Similarity	NPD2210	Approved
0.5967	Remote Similarity	NPD5633	Discontinued
0.5965	Remote Similarity	NPD4432	Discontinued
0.5965	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4739	Approved
0.596	Remote Similarity	NPD5631	Phase 3
0.5959	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD3948	Discontinued
0.5954	Remote Similarity	NPD2948	Discontinued
0.5951	Remote Similarity	NPD8325	Phase 3
0.5951	Remote Similarity	NPD8326	Phase 3
0.5951	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6874	Approved
0.5949	Remote Similarity	NPD5367	Discontinued
0.5948	Remote Similarity	NPD6360	Discontinued
0.5946	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD6786	Discontinued
0.5943	Remote Similarity	NPD6395	Phase 2
0.5943	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD3096	Phase 2
0.5939	Remote Similarity	NPD2670	Approved
0.5938	Remote Similarity	NPD7828	Discontinued
0.5933	Remote Similarity	NPD181	Approved
0.5932	Remote Similarity	NPD3558	Approved
0.5932	Remote Similarity	NPD3556	Approved
0.5932	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD3560	Approved
0.5932	Remote Similarity	NPD3557	Approved
0.5924	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD7508	Discontinued
0.5917	Remote Similarity	NPD2241	Approved
0.5916	Remote Similarity	NPD5994	Discontinued
0.5915	Remote Similarity	NPD4686	Approved
0.5915	Remote Similarity	NPD4684	Phase 3
0.5915	Remote Similarity	NPD5258	Approved
0.5915	Remote Similarity	NPD5260	Approved
0.5915	Remote Similarity	NPD4685	Phase 3
0.5914	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD2113	Approved
0.5909	Remote Similarity	NPD4479	Discontinued
0.5909	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6998	Discontinued
0.5904	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4586	Phase 3
0.5904	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD4125	Approved
0.5896	Remote Similarity	NPD7606	Phase 3
0.5896	Remote Similarity	NPD5982	Phase 2
0.5896	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5852	Approved
0.5895	Remote Similarity	NPD5851	Approved
0.5894	Remote Similarity	NPD3147	Approved
0.5894	Remote Similarity	NPD2658	Approved
0.5894	Remote Similarity	NPD2659	Approved
0.5894	Remote Similarity	NPD3150	Approved
0.5894	Remote Similarity	NPD3148	Approved
0.5894	Remote Similarity	NPD3149	Approved
0.5892	Remote Similarity	NPD7881	Approved
0.5886	Remote Similarity	NPD3538	Suspended
0.5882	Remote Similarity	NPD6070	Approved
0.5882	Remote Similarity	NPD6069	Approved
0.5882	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD5993	Phase 1
0.5872	Remote Similarity	NPD5941	Approved
0.5872	Remote Similarity	NPD5942	Approved
0.5871	Remote Similarity	NPD5981	Approved
0.5866	Remote Similarity	NPD7734	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