NPASS Compound

Structure

CID328141 OpenBabel06191716202D 29 32 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 4.3301 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 0.8660 -2.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 27 2 0 0 0 0 17 28 2 0 0 0 0 17 29 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 6 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 21 24 1 6 0 0 0 21 25 1 0 0 0 0 22 26 1 6 0 0 0 22 29 1 0 0 0 0 24 4 1 6 0 0 0 25 5 1 6 0 0 0 26 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.3
Volume:	442.488
LogP:	5.422
LogD:	4.542
LogS:	-5.528
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	4.695
Fsp3:	0.846
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.8
MDCK Permeability:	1.790433998394292e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	90.21451568603516%
Volume Distribution (VD):	1.295
Pgp-substrate:	7.59118127822876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.607
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	3.296
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.968
Carcinogencity:	0.09
Eye Corrosion:	0.991
Eye Irritation:	0.895
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC328141

Natural Product ID:	NPC328141
*Common Name:**	Hyrtial
IUPAC Name:	[(4aS,4bR,6R,6aR,10aS,10bR,12aS)-8-formyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate
Synonyms:	Hyrtial
Standard InCHIKey:	PTMXVTMFEPDKJQ-GAZMYWJLSA-N
Standard InCHI:	InChI=1S/C26H40O3/c1-17(28)29-22-14-21-24(4)12-7-11-23(2,3)19(24)10-13-25(21,5)20-9-8-18(16-27)15-26(20,22)6/h8,16,19-22H,7,9-15H2,1-6H3/t19-,20-,21+,22+,24-,25-,26+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2CC=C(C[C@@]12C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521070
PubChem CID:	126946
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO30702	Calanus helgolandicus	Species	Calanidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26364855]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO30702	Calanus helgolandicus	Species	Calanidae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO5239	Hyrtios erecta	Species	Thorectidae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	43.0	%	PMID[520735]

☑ 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 NPC328141 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	234
0.1-0.2	1557
0.2-0.3	5440
0.3-0.4	12746
0.4-0.5	9882
0.5-0.6	6213
0.6-0.7	4908
0.7-0.8	1503
0.8-0.85	185
0.85-0.9	20
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC269729
0.9545	High Similarity	NPC274417
0.913	High Similarity	NPC475392
0.913	High Similarity	NPC475202
0.913	High Similarity	NPC475385
0.908	High Similarity	NPC224145
0.8889	High Similarity	NPC474185
0.8864	High Similarity	NPC474925
0.8851	High Similarity	NPC329943
0.8851	High Similarity	NPC10005
0.8851	High Similarity	NPC91525
0.8851	High Similarity	NPC9892
0.8842	High Similarity	NPC282233
0.8842	High Similarity	NPC95585
0.8804	High Similarity	NPC471039
0.8791	High Similarity	NPC471040
0.8764	High Similarity	NPC469546
0.875	High Similarity	NPC30421
0.875	High Similarity	NPC162107
0.875	High Similarity	NPC46912
0.8736	High Similarity	NPC2709
0.871	High Similarity	NPC473456
0.8681	High Similarity	NPC79117
0.8652	High Similarity	NPC206060
0.8617	High Similarity	NPC471966
0.8605	High Similarity	NPC470813
0.8587	High Similarity	NPC74751
0.8571	High Similarity	NPC218301
0.8556	High Similarity	NPC475049
0.8495	Intermediate Similarity	NPC139570
0.8478	Intermediate Similarity	NPC214756
0.8478	Intermediate Similarity	NPC272075
0.8478	Intermediate Similarity	NPC295643
0.8462	Intermediate Similarity	NPC474728
0.8462	Intermediate Similarity	NPC101651
0.8462	Intermediate Similarity	NPC159748
0.8462	Intermediate Similarity	NPC113989
0.8462	Intermediate Similarity	NPC120840
0.8454	Intermediate Similarity	NPC254202
0.8444	Intermediate Similarity	NPC246708
0.8444	Intermediate Similarity	NPC474845
0.8444	Intermediate Similarity	NPC40552
0.8427	Intermediate Similarity	NPC325594
0.8404	Intermediate Similarity	NPC469545
0.8404	Intermediate Similarity	NPC61369
0.8404	Intermediate Similarity	NPC5532
0.8391	Intermediate Similarity	NPC142683
0.8391	Intermediate Similarity	NPC163236
0.837	Intermediate Similarity	NPC285184
0.837	Intermediate Similarity	NPC60755
0.837	Intermediate Similarity	NPC233455
0.837	Intermediate Similarity	NPC4036
0.837	Intermediate Similarity	NPC65120
0.837	Intermediate Similarity	NPC470590
0.837	Intermediate Similarity	NPC145067
0.837	Intermediate Similarity	NPC158030
0.837	Intermediate Similarity	NPC230064
0.837	Intermediate Similarity	NPC77099
0.8352	Intermediate Similarity	NPC470588
0.8352	Intermediate Similarity	NPC30522
0.8333	Intermediate Similarity	NPC293564
0.8333	Intermediate Similarity	NPC102683
0.8333	Intermediate Similarity	NPC51700
0.8333	Intermediate Similarity	NPC142415
0.8333	Intermediate Similarity	NPC242468
0.8333	Intermediate Similarity	NPC171203
0.8333	Intermediate Similarity	NPC18064
0.8333	Intermediate Similarity	NPC307426
0.8333	Intermediate Similarity	NPC98442
0.8333	Intermediate Similarity	NPC68160
0.8333	Intermediate Similarity	NPC130577
0.8333	Intermediate Similarity	NPC88716
0.8316	Intermediate Similarity	NPC292133
0.8316	Intermediate Similarity	NPC26413
0.8316	Intermediate Similarity	NPC226986
0.8316	Intermediate Similarity	NPC476768
0.8315	Intermediate Similarity	NPC474971
0.828	Intermediate Similarity	NPC49776
0.828	Intermediate Similarity	NPC298554
0.828	Intermediate Similarity	NPC63118
0.828	Intermediate Similarity	NPC151722
0.828	Intermediate Similarity	NPC474436
0.828	Intermediate Similarity	NPC86368
0.8276	Intermediate Similarity	NPC195334
0.8276	Intermediate Similarity	NPC290495
0.8265	Intermediate Similarity	NPC179208
0.8261	Intermediate Similarity	NPC474842
0.8261	Intermediate Similarity	NPC475965
0.8261	Intermediate Similarity	NPC152467
0.8247	Intermediate Similarity	NPC310981
0.8242	Intermediate Similarity	NPC474512
0.8242	Intermediate Similarity	NPC52169
0.8242	Intermediate Similarity	NPC17733
0.8242	Intermediate Similarity	NPC470629
0.8242	Intermediate Similarity	NPC290690
0.8242	Intermediate Similarity	NPC182797
0.8242	Intermediate Similarity	NPC181225
0.8242	Intermediate Similarity	NPC473242
0.8242	Intermediate Similarity	NPC473229
0.8235	Intermediate Similarity	NPC472300
0.8229	Intermediate Similarity	NPC194196
0.8229	Intermediate Similarity	NPC58942
0.8229	Intermediate Similarity	NPC478056
0.8229	Intermediate Similarity	NPC260149
0.8222	Intermediate Similarity	NPC95594
0.8222	Intermediate Similarity	NPC73038
0.8222	Intermediate Similarity	NPC195640
0.8222	Intermediate Similarity	NPC471042
0.8222	Intermediate Similarity	NPC477579
0.8222	Intermediate Similarity	NPC235341
0.8222	Intermediate Similarity	NPC72638
0.8211	Intermediate Similarity	NPC58052
0.8211	Intermediate Similarity	NPC98874
0.8211	Intermediate Similarity	NPC122324
0.8211	Intermediate Similarity	NPC111684
0.8211	Intermediate Similarity	NPC106425
0.8211	Intermediate Similarity	NPC151725
0.8202	Intermediate Similarity	NPC312660
0.82	Intermediate Similarity	NPC110496
0.8191	Intermediate Similarity	NPC471207
0.8191	Intermediate Similarity	NPC222047
0.8191	Intermediate Similarity	NPC23621
0.8191	Intermediate Similarity	NPC209868
0.8191	Intermediate Similarity	NPC169751
0.8191	Intermediate Similarity	NPC272635
0.8191	Intermediate Similarity	NPC474529
0.8191	Intermediate Similarity	NPC78580
0.8191	Intermediate Similarity	NPC296164
0.8191	Intermediate Similarity	NPC184006
0.8182	Intermediate Similarity	NPC286786
0.8161	Intermediate Similarity	NPC474956
0.8161	Intermediate Similarity	NPC267517
0.8152	Intermediate Similarity	NPC225585
0.8152	Intermediate Similarity	NPC474972
0.8152	Intermediate Similarity	NPC293048
0.8152	Intermediate Similarity	NPC59263
0.8152	Intermediate Similarity	NPC198664
0.8152	Intermediate Similarity	NPC95246
0.8152	Intermediate Similarity	NPC270768
0.8152	Intermediate Similarity	NPC234346
0.8152	Intermediate Similarity	NPC127689
0.8152	Intermediate Similarity	NPC290972
0.8152	Intermediate Similarity	NPC64872
0.8152	Intermediate Similarity	NPC274330
0.8152	Intermediate Similarity	NPC121798
0.8152	Intermediate Similarity	NPC263393
0.8152	Intermediate Similarity	NPC130520
0.8152	Intermediate Similarity	NPC143232
0.8152	Intermediate Similarity	NPC161751
0.8152	Intermediate Similarity	NPC25906
0.8152	Intermediate Similarity	NPC61543
0.8152	Intermediate Similarity	NPC50070
0.8144	Intermediate Similarity	NPC471041
0.8132	Intermediate Similarity	NPC71507
0.8125	Intermediate Similarity	NPC38530
0.8125	Intermediate Similarity	NPC84335
0.8125	Intermediate Similarity	NPC23680
0.8125	Intermediate Similarity	NPC89225
0.8119	Intermediate Similarity	NPC189075
0.8119	Intermediate Similarity	NPC275539
0.8111	Intermediate Similarity	NPC323765
0.8105	Intermediate Similarity	NPC473240
0.8105	Intermediate Similarity	NPC195715
0.8105	Intermediate Similarity	NPC23241
0.8105	Intermediate Similarity	NPC474727
0.8105	Intermediate Similarity	NPC148523
0.809	Intermediate Similarity	NPC132386
0.809	Intermediate Similarity	NPC307258
0.8085	Intermediate Similarity	NPC136313
0.8085	Intermediate Similarity	NPC307335
0.8085	Intermediate Similarity	NPC74855
0.8081	Intermediate Similarity	NPC478057
0.8081	Intermediate Similarity	NPC95899
0.8068	Intermediate Similarity	NPC471898
0.8068	Intermediate Similarity	NPC475665
0.8068	Intermediate Similarity	NPC108476
0.8065	Intermediate Similarity	NPC120968
0.8065	Intermediate Similarity	NPC210037
0.8065	Intermediate Similarity	NPC291028
0.8065	Intermediate Similarity	NPC130278
0.8065	Intermediate Similarity	NPC7260
0.8065	Intermediate Similarity	NPC227467
0.8065	Intermediate Similarity	NPC86372
0.8065	Intermediate Similarity	NPC273621
0.8065	Intermediate Similarity	NPC8062
0.8065	Intermediate Similarity	NPC290614
0.8065	Intermediate Similarity	NPC172361
0.8065	Intermediate Similarity	NPC85173
0.8065	Intermediate Similarity	NPC18872
0.8065	Intermediate Similarity	NPC126369
0.8065	Intermediate Similarity	NPC470589
0.8065	Intermediate Similarity	NPC471896
0.8065	Intermediate Similarity	NPC477872
0.8065	Intermediate Similarity	NPC111110
0.8043	Intermediate Similarity	NPC80335
0.8043	Intermediate Similarity	NPC472802
0.8041	Intermediate Similarity	NPC475876
0.8041	Intermediate Similarity	NPC188833
0.8041	Intermediate Similarity	NPC176845
0.8039	Intermediate Similarity	NPC112457

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 NPC328141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1809
0.2-0.3	3961
0.3-0.4	2067
0.4-0.5	672
0.5-0.6	193
0.6-0.7	151
0.7-0.8	71
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3573	Approved
0.8587	High Similarity	NPD7900	Approved
0.8587	High Similarity	NPD7901	Clinical (unspecified phase)
0.8587	High Similarity	NPD7748	Approved
0.8444	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD7515	Phase 2
0.8316	Intermediate Similarity	NPD7902	Approved
0.8222	Intermediate Similarity	NPD7146	Approved
0.8222	Intermediate Similarity	NPD6409	Approved
0.8222	Intermediate Similarity	NPD6684	Approved
0.8222	Intermediate Similarity	NPD7521	Approved
0.8222	Intermediate Similarity	NPD5330	Approved
0.8222	Intermediate Similarity	NPD7334	Approved
0.8043	Intermediate Similarity	NPD6903	Approved
0.7979	Intermediate Similarity	NPD6079	Approved
0.7957	Intermediate Similarity	NPD5328	Approved
0.7849	Intermediate Similarity	NPD6672	Approved
0.7849	Intermediate Similarity	NPD5737	Approved
0.7767	Intermediate Similarity	NPD6899	Approved
0.7767	Intermediate Similarity	NPD6881	Approved
0.7745	Intermediate Similarity	NPD6675	Approved
0.7745	Intermediate Similarity	NPD6402	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD5697	Approved
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7634	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD7290	Approved
0.7619	Intermediate Similarity	NPD7102	Approved
0.7619	Intermediate Similarity	NPD6883	Approved
0.7596	Intermediate Similarity	NPD6011	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7582	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD6008	Approved
0.7551	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD8130	Phase 1
0.7547	Intermediate Similarity	NPD6869	Approved
0.7547	Intermediate Similarity	NPD6649	Approved
0.7547	Intermediate Similarity	NPD6847	Approved
0.7547	Intermediate Similarity	NPD6650	Approved
0.7547	Intermediate Similarity	NPD6617	Approved
0.7527	Intermediate Similarity	NPD1694	Approved
0.7527	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.7524	Intermediate Similarity	NPD6372	Approved
0.7524	Intermediate Similarity	NPD6373	Approved
0.7524	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD6012	Approved
0.7524	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD8297	Approved
0.7475	Intermediate Similarity	NPD7732	Phase 3
0.7475	Intermediate Similarity	NPD5221	Approved
0.7475	Intermediate Similarity	NPD5222	Approved
0.7475	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7423	Intermediate Similarity	NPD8034	Phase 2
0.7423	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD5173	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.7396	Intermediate Similarity	NPD6673	Approved
0.7383	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD6001	Approved
0.7263	Intermediate Similarity	NPD6098	Approved
0.7255	Intermediate Similarity	NPD5285	Approved
0.7255	Intermediate Similarity	NPD4696	Approved
0.7255	Intermediate Similarity	NPD5286	Approved
0.7253	Intermediate Similarity	NPD7645	Phase 2
0.7245	Intermediate Similarity	NPD6411	Approved
0.7234	Intermediate Similarity	NPD3666	Approved
0.7234	Intermediate Similarity	NPD4786	Approved
0.7234	Intermediate Similarity	NPD3665	Phase 1
0.7234	Intermediate Similarity	NPD3133	Approved
0.7228	Intermediate Similarity	NPD6083	Phase 2
0.7228	Intermediate Similarity	NPD6084	Phase 2
0.7228	Intermediate Similarity	NPD4755	Approved
0.7216	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3667	Approved
0.7184	Intermediate Similarity	NPD5223	Approved
0.7172	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD6335	Approved
0.7129	Intermediate Similarity	NPD7614	Phase 1
0.7117	Intermediate Similarity	NPD6274	Approved
0.7115	Intermediate Similarity	NPD5211	Phase 2
0.7115	Intermediate Similarity	NPD5224	Approved
0.7115	Intermediate Similarity	NPD5225	Approved
0.7115	Intermediate Similarity	NPD5226	Approved
0.7115	Intermediate Similarity	NPD4633	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD4700	Approved
0.708	Intermediate Similarity	NPD7100	Approved
0.708	Intermediate Similarity	NPD7101	Approved
0.7071	Intermediate Similarity	NPD6050	Approved
0.7071	Intermediate Similarity	NPD5693	Phase 1
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD6317	Approved
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7048	Intermediate Similarity	NPD5174	Approved
0.7048	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD6314	Approved
0.6991	Remote Similarity	NPD6313	Approved
0.699	Remote Similarity	NPD5696	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6983	Remote Similarity	NPD8328	Phase 3
0.6981	Remote Similarity	NPD5141	Approved
0.697	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD5692	Phase 3
0.6932	Remote Similarity	NPD4691	Approved
0.6907	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6009	Approved
0.69	Remote Similarity	NPD5694	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6887	Remote Similarity	NPD4754	Approved
0.687	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6838	Remote Similarity	NPD7604	Phase 2
0.6833	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD4225	Approved
0.6818	Remote Similarity	NPD4137	Phase 3
0.681	Remote Similarity	NPD5983	Phase 2
0.681	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD6909	Approved
0.6804	Remote Similarity	NPD5329	Approved
0.6792	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD5128	Approved
0.6789	Remote Similarity	NPD4729	Approved
0.6789	Remote Similarity	NPD5168	Approved
0.6789	Remote Similarity	NPD4730	Approved
0.6786	Remote Similarity	NPD6858	Approved
0.6786	Remote Similarity	NPD7094	Approved
0.678	Remote Similarity	NPD7492	Approved
0.6759	Remote Similarity	NPD4768	Approved
0.6759	Remote Similarity	NPD4767	Approved
0.6742	Remote Similarity	NPD4747	Approved
0.6735	Remote Similarity	NPD5279	Phase 3
0.6724	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6336	Discontinued
0.6723	Remote Similarity	NPD6616	Approved
0.6703	Remote Similarity	NPD4058	Approved
0.6701	Remote Similarity	NPD4197	Approved
0.67	Remote Similarity	NPD6051	Approved
0.67	Remote Similarity	NPD4753	Phase 2
0.6697	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6632	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD8039	Approved
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD5216	Approved
0.6607	Remote Similarity	NPD5127	Approved
0.6607	Remote Similarity	NPD5217	Approved
0.6598	Remote Similarity	NPD4788	Approved
0.6596	Remote Similarity	NPD3617	Approved
0.6581	Remote Similarity	NPD6059	Approved
0.6577	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6052	Approved
0.6569	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD4519	Discontinued
0.6566	Remote Similarity	NPD4689	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6566	Remote Similarity	NPD4623	Approved
0.6562	Remote Similarity	NPD8028	Phase 2
0.6559	Remote Similarity	NPD6117	Approved
0.6545	Remote Similarity	NPD6614	Approved
0.6538	Remote Similarity	NPD4629	Approved
0.6538	Remote Similarity	NPD5210	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