NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	376.3
Volume:	425.008
LogP:	7.613
LogD:	4.704
LogS:	-6.161
# Rotatable Bonds:	11
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	3.859
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.585
MDCK Permeability:	1.5833602446946315e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	98.2439193725586%
Volume Distribution (VD):	1.817
Pgp-substrate:	1.8599047660827637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.322
CYP2C19-inhibitor:	0.467
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.646
CYP2D6-inhibitor:	0.37
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	10.232
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.505
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.351
Skin Sensitization:	0.963
Carcinogencity:	0.166
Eye Corrosion:	0.862
Eye Irritation:	0.976
Respiratory Toxicity:	0.408

Download Data

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

Natural Product: NPC477770

Natural Product ID:	NPC477770
*Common Name:**	(3S)-3,4alpha,6beta-Trimethyl-6-[2-methyl-10-phenyldecyl]-1,2-dioxane-3alpha-ol
IUPAC Name:	(3S,4R,6S)-3,4,6-trimethyl-6-(2-methyl-10-phenyldecyl)dioxan-3-ol
Synonyms:
Standard InCHIKey:	YSHAXSNVWDJIDZ-YEWCTYBBSA-N
Standard InCHI:	InChI=1S/C24H40O3/c1-20(18-23(3)19-21(2)24(4,25)27-26-23)14-10-7-5-6-8-11-15-22-16-12-9-13-17-22/h9,12-13,16-17,20-21,25H,5-8,10-11,14-15,18-19H2,1-4H3/t20?,21-,23+,24+/m1/s1
SMILES:	C[C@@H]1C[C@](OO[C@]1(C)O)(C)CC(C)CCCCCCCCC2=CC=CC=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44254885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[11720540]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738400]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam	n.a.	PMID[19618913]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20235550]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[23186727]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760075]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722495]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	PMID[19618913]

☑ 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 NPC477770 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	147
0.1-0.2	1083
0.2-0.3	2786
0.3-0.4	13097
0.4-0.5	18355
0.5-0.6	5908
0.6-0.7	1213
0.7-0.8	104
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC477767
0.8481	Intermediate Similarity	NPC189371
0.8214	Intermediate Similarity	NPC121478
0.8214	Intermediate Similarity	NPC73637
0.8193	Intermediate Similarity	NPC164449
0.8193	Intermediate Similarity	NPC184030
0.8023	Intermediate Similarity	NPC95429
0.7976	Intermediate Similarity	NPC328178
0.7952	Intermediate Similarity	NPC224544
0.7931	Intermediate Similarity	NPC99482
0.7907	Intermediate Similarity	NPC44830
0.7882	Intermediate Similarity	NPC133050
0.7875	Intermediate Similarity	NPC208302
0.7872	Intermediate Similarity	NPC271475
0.7841	Intermediate Similarity	NPC474211
0.7791	Intermediate Similarity	NPC283012
0.7791	Intermediate Similarity	NPC475199
0.7727	Intermediate Similarity	NPC474354
0.7727	Intermediate Similarity	NPC475710
0.7692	Intermediate Similarity	NPC84288
0.7683	Intermediate Similarity	NPC108218
0.7647	Intermediate Similarity	NPC469894
0.764	Intermediate Similarity	NPC243166
0.7629	Intermediate Similarity	NPC475978
0.7629	Intermediate Similarity	NPC474820
0.7614	Intermediate Similarity	NPC304538
0.7614	Intermediate Similarity	NPC168855
0.7582	Intermediate Similarity	NPC1793
0.7558	Intermediate Similarity	NPC127343
0.7556	Intermediate Similarity	NPC322387
0.7526	Intermediate Similarity	NPC225079
0.7526	Intermediate Similarity	NPC94487
0.75	Intermediate Similarity	NPC86670
0.75	Intermediate Similarity	NPC274455
0.75	Intermediate Similarity	NPC70940
0.7473	Intermediate Similarity	NPC477693
0.7473	Intermediate Similarity	NPC477704
0.7471	Intermediate Similarity	NPC242628
0.7419	Intermediate Similarity	NPC141607
0.7419	Intermediate Similarity	NPC187725
0.7419	Intermediate Similarity	NPC220596
0.7403	Intermediate Similarity	NPC210849
0.7396	Intermediate Similarity	NPC473388
0.7386	Intermediate Similarity	NPC103387
0.7386	Intermediate Similarity	NPC103326
0.7386	Intermediate Similarity	NPC99394
0.7386	Intermediate Similarity	NPC329319
0.7386	Intermediate Similarity	NPC87299
0.7356	Intermediate Similarity	NPC309279
0.7347	Intermediate Similarity	NPC266343
0.7347	Intermediate Similarity	NPC264728
0.7333	Intermediate Similarity	NPC95965
0.7327	Intermediate Similarity	NPC329705
0.7327	Intermediate Similarity	NPC474111
0.732	Intermediate Similarity	NPC120393
0.7303	Intermediate Similarity	NPC270507
0.7303	Intermediate Similarity	NPC285773
0.73	Intermediate Similarity	NPC472221
0.73	Intermediate Similarity	NPC472222
0.7292	Intermediate Similarity	NPC26244
0.7283	Intermediate Similarity	NPC329064
0.7273	Intermediate Similarity	NPC117180
0.7263	Intermediate Similarity	NPC210497
0.7263	Intermediate Similarity	NPC306884
0.7263	Intermediate Similarity	NPC94139
0.7263	Intermediate Similarity	NPC147284
0.7263	Intermediate Similarity	NPC3358
0.7263	Intermediate Similarity	NPC162314
0.7253	Intermediate Similarity	NPC93843
0.7241	Intermediate Similarity	NPC170484
0.7234	Intermediate Similarity	NPC86987
0.7234	Intermediate Similarity	NPC55561
0.7229	Intermediate Similarity	NPC155429
0.7222	Intermediate Similarity	NPC267704
0.7216	Intermediate Similarity	NPC324602
0.7216	Intermediate Similarity	NPC469890
0.7216	Intermediate Similarity	NPC469892
0.7216	Intermediate Similarity	NPC469891
0.7204	Intermediate Similarity	NPC231591
0.72	Intermediate Similarity	NPC19856
0.72	Intermediate Similarity	NPC247976
0.7191	Intermediate Similarity	NPC323103
0.7188	Intermediate Similarity	NPC206764
0.7188	Intermediate Similarity	NPC151715
0.7188	Intermediate Similarity	NPC58674
0.7179	Intermediate Similarity	NPC135924
0.7172	Intermediate Similarity	NPC133809
0.7172	Intermediate Similarity	NPC248396
0.7172	Intermediate Similarity	NPC136810
0.7172	Intermediate Similarity	NPC129373
0.7172	Intermediate Similarity	NPC128248
0.7172	Intermediate Similarity	NPC48730
0.7159	Intermediate Similarity	NPC121800
0.7159	Intermediate Similarity	NPC192623
0.7157	Intermediate Similarity	NPC244933
0.7157	Intermediate Similarity	NPC477251
0.7157	Intermediate Similarity	NPC85560
0.7143	Intermediate Similarity	NPC262826
0.7129	Intermediate Similarity	NPC47286
0.7129	Intermediate Similarity	NPC329282
0.7129	Intermediate Similarity	NPC19136
0.7128	Intermediate Similarity	NPC318325
0.7128	Intermediate Similarity	NPC242240
0.7128	Intermediate Similarity	NPC159178
0.7128	Intermediate Similarity	NPC78041
0.7128	Intermediate Similarity	NPC121872
0.7128	Intermediate Similarity	NPC141139
0.7128	Intermediate Similarity	NPC74936
0.7128	Intermediate Similarity	NPC209764
0.7128	Intermediate Similarity	NPC123273
0.7128	Intermediate Similarity	NPC471307
0.7128	Intermediate Similarity	NPC172128
0.7128	Intermediate Similarity	NPC280347
0.7128	Intermediate Similarity	NPC258219
0.7128	Intermediate Similarity	NPC177420
0.7125	Intermediate Similarity	NPC155172
0.7125	Intermediate Similarity	NPC32312
0.7125	Intermediate Similarity	NPC198023
0.7113	Intermediate Similarity	NPC25565
0.7113	Intermediate Similarity	NPC469893
0.7113	Intermediate Similarity	NPC32714
0.7111	Intermediate Similarity	NPC172984
0.71	Intermediate Similarity	NPC474112
0.7089	Intermediate Similarity	NPC22786
0.7087	Intermediate Similarity	NPC21929
0.7071	Intermediate Similarity	NPC54647
0.7071	Intermediate Similarity	NPC260775
0.7053	Intermediate Similarity	NPC192
0.7045	Intermediate Similarity	NPC272260
0.7041	Intermediate Similarity	NPC132271
0.7041	Intermediate Similarity	NPC292730
0.7041	Intermediate Similarity	NPC475439
0.7041	Intermediate Similarity	NPC216520
0.7041	Intermediate Similarity	NPC473501
0.7041	Intermediate Similarity	NPC82664
0.703	Intermediate Similarity	NPC329556
0.703	Intermediate Similarity	NPC108497
0.7021	Intermediate Similarity	NPC113460
0.7021	Intermediate Similarity	NPC470877
0.7021	Intermediate Similarity	NPC25493
0.7019	Intermediate Similarity	NPC475006
0.7013	Intermediate Similarity	NPC120441
0.7013	Intermediate Similarity	NPC300345
0.7013	Intermediate Similarity	NPC65873
0.7013	Intermediate Similarity	NPC212114
0.7011	Intermediate Similarity	NPC9796
0.7011	Intermediate Similarity	NPC66655
0.701	Intermediate Similarity	NPC76938
0.701	Intermediate Similarity	NPC161972
0.701	Intermediate Similarity	NPC303045
0.7	Intermediate Similarity	NPC88566
0.7	Intermediate Similarity	NPC45756
0.7	Intermediate Similarity	NPC469481
0.7	Intermediate Similarity	NPC72729
0.7	Intermediate Similarity	NPC70677
0.7	Intermediate Similarity	NPC130756
0.7	Intermediate Similarity	NPC158623
0.7	Intermediate Similarity	NPC12931
0.699	Remote Similarity	NPC155072
0.699	Remote Similarity	NPC100767
0.699	Remote Similarity	NPC469913
0.6989	Remote Similarity	NPC96625
0.6989	Remote Similarity	NPC194326
0.6979	Remote Similarity	NPC45040
0.6979	Remote Similarity	NPC304541
0.6979	Remote Similarity	NPC270547
0.6979	Remote Similarity	NPC314690
0.697	Remote Similarity	NPC329387
0.697	Remote Similarity	NPC152097
0.697	Remote Similarity	NPC474073
0.697	Remote Similarity	NPC317280
0.697	Remote Similarity	NPC475078
0.6966	Remote Similarity	NPC477703
0.6962	Remote Similarity	NPC54368
0.6962	Remote Similarity	NPC246588
0.6962	Remote Similarity	NPC150196
0.6962	Remote Similarity	NPC248705
0.6961	Remote Similarity	NPC194390
0.6961	Remote Similarity	NPC224610
0.6961	Remote Similarity	NPC113326
0.6961	Remote Similarity	NPC88267
0.6961	Remote Similarity	NPC323810
0.6961	Remote Similarity	NPC56168
0.6957	Remote Similarity	NPC3210
0.6947	Remote Similarity	NPC26224
0.6941	Remote Similarity	NPC54269
0.6932	Remote Similarity	NPC103488
0.6931	Remote Similarity	NPC477685
0.6931	Remote Similarity	NPC80800
0.6931	Remote Similarity	NPC51015
0.6923	Remote Similarity	NPC320439
0.6923	Remote Similarity	NPC288903
0.6923	Remote Similarity	NPC472980
0.6923	Remote Similarity	NPC27252
0.6923	Remote Similarity	NPC472979
0.6915	Remote Similarity	NPC23167
0.6915	Remote Similarity	NPC407
0.6915	Remote Similarity	NPC307235
0.6915	Remote Similarity	NPC325441
0.6907	Remote Similarity	NPC471309

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 NPC477770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	846
0.2-0.3	1331
0.3-0.4	3274
0.4-0.5	2303
0.5-0.6	1002
0.6-0.7	231
0.7-0.8	14
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
0.7978	Intermediate Similarity	NPD5347	Phase 2
0.7978	Intermediate Similarity	NPD5346	Phase 2
0.7826	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD4793	Discontinued
0.7582	Intermediate Similarity	NPD800	Approved
0.75	Intermediate Similarity	NPD1090	Approved
0.75	Intermediate Similarity	NPD1086	Approved
0.75	Intermediate Similarity	NPD1089	Approved
0.7473	Intermediate Similarity	NPD1101	Approved
0.7471	Intermediate Similarity	NPD226	Approved
0.7423	Intermediate Similarity	NPD2066	Phase 3
0.7368	Intermediate Similarity	NPD1693	Approved
0.7368	Intermediate Similarity	NPD4814	Discontinued
0.734	Intermediate Similarity	NPD1088	Approved
0.7303	Intermediate Similarity	NPD9491	Approved
0.7292	Intermediate Similarity	NPD2859	Approved
0.7292	Intermediate Similarity	NPD2860	Approved
0.7273	Intermediate Similarity	NPD4818	Approved
0.7273	Intermediate Similarity	NPD4817	Approved
0.7263	Intermediate Similarity	NPD3719	Approved
0.7263	Intermediate Similarity	NPD3718	Approved
0.7245	Intermediate Similarity	NPD3020	Approved
0.72	Intermediate Similarity	NPD5765	Approved
0.7188	Intermediate Similarity	NPD2933	Approved
0.7188	Intermediate Similarity	NPD2934	Approved
0.7174	Intermediate Similarity	NPD1087	Approved
0.7157	Intermediate Similarity	NPD6685	Approved
0.7143	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3673	Approved
0.7128	Intermediate Similarity	NPD3672	Approved
0.7126	Intermediate Similarity	NPD227	Approved
0.7126	Intermediate Similarity	NPD225	Approved
0.7111	Intermediate Similarity	NPD3971	Phase 1
0.7097	Intermediate Similarity	NPD531	Approved
0.7083	Intermediate Similarity	NPD1409	Phase 3
0.7083	Intermediate Similarity	NPD845	Approved
0.7053	Intermediate Similarity	NPD530	Approved
0.7053	Intermediate Similarity	NPD1239	Approved
0.7041	Intermediate Similarity	NPD1565	Approved
0.7041	Intermediate Similarity	NPD1566	Phase 3
0.7041	Intermediate Similarity	NPD1564	Approved
0.703	Intermediate Similarity	NPD1930	Approved
0.703	Intermediate Similarity	NPD3681	Approved
0.703	Intermediate Similarity	NPD6647	Phase 2
0.703	Intermediate Similarity	NPD1929	Approved
0.703	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4231	Approved
0.703	Intermediate Similarity	NPD3683	Approved
0.703	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4229	Approved
0.7011	Intermediate Similarity	NPD9294	Approved
0.7	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6690	Approved
0.6979	Remote Similarity	NPD752	Approved
0.6961	Remote Similarity	NPD5909	Discontinued
0.6939	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD1066	Discontinued
0.6907	Remote Similarity	NPD719	Approved
0.6907	Remote Similarity	NPD720	Approved
0.6887	Remote Similarity	NPD4254	Approved
0.6887	Remote Similarity	NPD4253	Approved
0.6863	Remote Similarity	NPD4658	Approved
0.6863	Remote Similarity	NPD3680	Approved
0.6863	Remote Similarity	NPD3682	Approved
0.6863	Remote Similarity	NPD4656	Approved
0.6863	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD9490	Approved
0.6837	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6049	Phase 2
0.6809	Remote Similarity	NPD9538	Approved
0.679	Remote Similarity	NPD675	Discontinued
0.6782	Remote Similarity	NPD9716	Approved
0.6768	Remote Similarity	NPD844	Approved
0.6768	Remote Similarity	NPD1989	Approved
0.6765	Remote Similarity	NPD4719	Phase 2
0.6765	Remote Similarity	NPD1932	Approved
0.6762	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6406	Approved
0.6759	Remote Similarity	NPD7635	Approved
0.6735	Remote Similarity	NPD1563	Approved
0.6733	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1067	Discontinued
0.6731	Remote Similarity	NPD5048	Discontinued
0.6729	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6671	Approved
0.67	Remote Similarity	NPD288	Approved
0.67	Remote Similarity	NPD1875	Phase 1
0.6699	Remote Similarity	NPD1415	Approved
0.6698	Remote Similarity	NPD4720	Approved
0.6698	Remote Similarity	NPD2329	Discontinued
0.6698	Remote Similarity	NPD4717	Approved
0.6698	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4718	Approved
0.6667	Remote Similarity	NPD7343	Discovery
0.6667	Remote Similarity	NPD3772	Phase 3
0.6667	Remote Similarity	NPD1616	Discontinued
0.6667	Remote Similarity	NPD7344	Phase 1
0.6667	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3022	Approved
0.6636	Remote Similarity	NPD3021	Approved
0.6634	Remote Similarity	NPD5926	Approved
0.6634	Remote Similarity	NPD253	Approved
0.6633	Remote Similarity	NPD7631	Approved
0.6604	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4119	Approved
0.6602	Remote Similarity	NPD940	Approved
0.6602	Remote Similarity	NPD846	Approved
0.66	Remote Similarity	NPD1809	Phase 2
0.6596	Remote Similarity	NPD111	Approved
0.6588	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3644	Approved
0.6574	Remote Similarity	NPD3643	Approved
0.6574	Remote Similarity	NPD3642	Approved
0.6574	Remote Similarity	NPD2201	Approved
0.6571	Remote Similarity	NPD5717	Approved
0.6569	Remote Similarity	NPD7798	Approved
0.6545	Remote Similarity	NPD2229	Approved
0.6545	Remote Similarity	NPD2234	Approved
0.6545	Remote Similarity	NPD2650	Approved
0.6545	Remote Similarity	NPD2228	Approved
0.6545	Remote Similarity	NPD2652	Approved
0.6535	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7609	Phase 3
0.6505	Remote Similarity	NPD3028	Approved
0.6486	Remote Similarity	NPD2629	Approved
0.6481	Remote Similarity	NPD5237	Approved
0.6481	Remote Similarity	NPD5235	Approved
0.6481	Remote Similarity	NPD4750	Phase 3
0.6481	Remote Similarity	NPD1317	Discontinued
0.6481	Remote Similarity	NPD5240	Approved
0.6481	Remote Similarity	NPD5236	Approved
0.6481	Remote Similarity	NPD5239	Approved
0.6471	Remote Similarity	NPD9495	Approved
0.6465	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1814	Approved
0.6465	Remote Similarity	NPD1812	Approved
0.646	Remote Similarity	NPD7522	Discontinued
0.646	Remote Similarity	NPD7610	Discontinued
0.6435	Remote Similarity	NPD7725	Approved
0.6429	Remote Similarity	NPD7508	Discontinued
0.6429	Remote Similarity	NPD3317	Approved
0.6429	Remote Similarity	NPD4198	Discontinued
0.6422	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7741	Discontinued
0.6396	Remote Similarity	NPD6010	Discontinued
0.6395	Remote Similarity	NPD1673	Approved
0.6373	Remote Similarity	NPD9566	Approved
0.6372	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2500	Approved
0.6364	Remote Similarity	NPD3651	Discontinued
0.6364	Remote Similarity	NPD2499	Approved
0.6355	Remote Similarity	NPD5704	Approved
0.6355	Remote Similarity	NPD1444	Approved
0.6355	Remote Similarity	NPD5706	Approved
0.6355	Remote Similarity	NPD1445	Approved
0.6355	Remote Similarity	NPD5705	Approved
0.6346	Remote Similarity	NPD2552	Approved
0.6346	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2558	Approved
0.6346	Remote Similarity	NPD2549	Approved
0.6346	Remote Similarity	NPD2550	Approved
0.6346	Remote Similarity	NPD2555	Approved
0.6346	Remote Similarity	NPD2553	Approved
0.6344	Remote Similarity	NPD9250	Approved
0.6344	Remote Similarity	NPD942	Approved
0.6344	Remote Similarity	NPD3035	Approved
0.6344	Remote Similarity	NPD4026	Approved
0.6344	Remote Similarity	NPD4027	Approved
0.6337	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1792	Phase 2
0.633	Remote Similarity	NPD5278	Discontinued
0.6325	Remote Similarity	NPD4807	Approved
0.6325	Remote Similarity	NPD4806	Approved
0.6321	Remote Similarity	NPD1237	Approved
0.6311	Remote Similarity	NPD9609	Approved
0.6311	Remote Similarity	NPD9612	Approved
0.6311	Remote Similarity	NPD4117	Approved
0.6311	Remote Similarity	NPD4263	Approved
0.6311	Remote Similarity	NPD9611	Approved
0.6311	Remote Similarity	NPD4813	Approved
0.6311	Remote Similarity	NPD1724	Approved
0.631	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6858	Approved
0.6306	Remote Similarity	NPD7094	Approved
0.6293	Remote Similarity	NPD5125	Phase 3
0.6293	Remote Similarity	NPD5306	Approved
0.6293	Remote Similarity	NPD5126	Approved
0.6293	Remote Similarity	NPD5305	Approved
0.6289	Remote Similarity	NPD1282	Approved
0.6286	Remote Similarity	NPD855	Approved
0.6286	Remote Similarity	NPD854	Approved
0.6286	Remote Similarity	NPD4188	Approved
0.6286	Remote Similarity	NPD4189	Approved
0.6286	Remote Similarity	NPD5716	Approved
0.6277	Remote Similarity	NPD4170	Approved
0.6277	Remote Similarity	NPD4701	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