NPASS Compound

Structure

CID91251 OpenBabel06191715432D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.3660 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0804 -0.2480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4049 -5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8559 -2.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4927 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4927 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8559 -1.5570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3171 -1.0570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3171 -2.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9049 -2.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8070 -1.2480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4049 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 11 26 1 0 0 0 0 11 31 1 0 0 0 0 13 17 1 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 35 1 0 0 0 0 17 30 1 1 0 0 0 18 10 1 1 0 0 0 18 21 1 0 0 0 0 18 34 1 0 0 0 0 19 12 1 1 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.25
Volume:	492.592
LogP:	2.352
LogD:	1.8
LogS:	-3.591
# Rotatable Bonds:	7
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	6.72
Fsp3:	0.808
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:	-5.127
MDCK Permeability:	6.452700472436845e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	38.199256896972656%
Volume Distribution (VD):	1.373
Pgp-substrate:	40.18678283691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.313
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	2.821
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.651
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.251
Carcinogencity:	0.118
Eye Corrosion:	0.007
Eye Irritation:	0.013
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC91251

Natural Product ID:	NPC91251
*Common Name:**	IJXBJCLCYUSOPN-YRLDIHFHSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Klymollin C
Standard InCHIKey:	IJXBJCLCYUSOPN-YRLDIHFHSA-N
Standard InCHI:	InChI=1S/C26H38O9/c1-12(2)19-20-21(26(11-31-26)24(33-15(5)28)22(19)32-14(4)27)18-10-13(3)17(30)8-9-25(7,23(20)34-18)35-16(6)29/h12,17-24,30H,3,8-11H2,1-2,4-7H3/t17-,18+,19+,20+,21+,22-,23+,24-,25+,26+/m0/s1
SMILES:	CC(C)[C@@H]1[C@@H]2[C@@H]([C@H]3CC(=C)[C@H](CC[C@](C)([C@@H]2O3)OC(=O)C)O)[C@]2(CO2)[C@H]([C@H]1OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923037
PubChem CID:	56655567
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0004153] Cladiellane diterpenoids

*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
NPO16055	Klyxum molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22004052]
NPO16055	Klyxum molle	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24020806]
NPO16055	Klyxum molle	Species	Alcyoniidae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	42.1	%	PMID[480864]

☑ 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 NPC91251 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	204
0.1-0.2	1847
0.2-0.3	5821
0.3-0.4	14211
0.4-0.5	9166
0.5-0.6	7895
0.6-0.7	3204
0.7-0.8	311
0.8-0.85	20
0.85-0.9	8
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC161560
0.9647	High Similarity	NPC470260
0.9647	High Similarity	NPC75443
0.9529	High Similarity	NPC44538
0.9412	High Similarity	NPC475684
0.931	High Similarity	NPC291875
0.9205	High Similarity	NPC471378
0.9205	High Similarity	NPC312471
0.9195	High Similarity	NPC476723
0.9195	High Similarity	NPC92370
0.9195	High Similarity	NPC476724
0.907	High Similarity	NPC471379
0.907	High Similarity	NPC196911
0.9059	High Similarity	NPC5958
0.8889	High Similarity	NPC122057
0.8824	High Similarity	NPC77003
0.8681	High Similarity	NPC312805
0.8636	High Similarity	NPC476725
0.8621	High Similarity	NPC127917
0.8605	High Similarity	NPC118116
0.8488	Intermediate Similarity	NPC186594
0.8438	Intermediate Similarity	NPC272223
0.8409	Intermediate Similarity	NPC239308
0.8384	Intermediate Similarity	NPC470263
0.8333	Intermediate Similarity	NPC322922
0.8333	Intermediate Similarity	NPC321812
0.8295	Intermediate Similarity	NPC216800
0.8295	Intermediate Similarity	NPC103171
0.828	Intermediate Similarity	NPC8729
0.8256	Intermediate Similarity	NPC43463
0.8229	Intermediate Similarity	NPC111348
0.8229	Intermediate Similarity	NPC473244
0.8229	Intermediate Similarity	NPC472998
0.8211	Intermediate Similarity	NPC476720
0.8211	Intermediate Similarity	NPC241047
0.8182	Intermediate Similarity	NPC211049
0.8125	Intermediate Similarity	NPC111834
0.8125	Intermediate Similarity	NPC306797
0.8125	Intermediate Similarity	NPC169270
0.8125	Intermediate Similarity	NPC292718
0.8046	Intermediate Similarity	NPC264610
0.8023	Intermediate Similarity	NPC136424
0.8023	Intermediate Similarity	NPC329626
0.8023	Intermediate Similarity	NPC293223
0.8021	Intermediate Similarity	NPC469583
0.798	Intermediate Similarity	NPC98225
0.7979	Intermediate Similarity	NPC10274
0.7978	Intermediate Similarity	NPC119922
0.7978	Intermediate Similarity	NPC116320
0.7957	Intermediate Similarity	NPC309656
0.7938	Intermediate Similarity	NPC284194
0.7938	Intermediate Similarity	NPC472997
0.7938	Intermediate Similarity	NPC471765
0.7938	Intermediate Similarity	NPC211810
0.7938	Intermediate Similarity	NPC221801
0.7938	Intermediate Similarity	NPC472996
0.7935	Intermediate Similarity	NPC214315
0.7935	Intermediate Similarity	NPC228593
0.7935	Intermediate Similarity	NPC235196
0.7907	Intermediate Similarity	NPC36479
0.79	Intermediate Similarity	NPC470972
0.7895	Intermediate Similarity	NPC41838
0.7895	Intermediate Similarity	NPC208839
0.7895	Intermediate Similarity	NPC219516
0.7879	Intermediate Similarity	NPC188968
0.7879	Intermediate Similarity	NPC79303
0.7857	Intermediate Similarity	NPC274793
0.7841	Intermediate Similarity	NPC52755
0.7841	Intermediate Similarity	NPC191345
0.7841	Intermediate Similarity	NPC252483
0.7835	Intermediate Similarity	NPC86893
0.7835	Intermediate Similarity	NPC292178
0.7822	Intermediate Similarity	NPC61442
0.7812	Intermediate Similarity	NPC26046
0.78	Intermediate Similarity	NPC49532
0.78	Intermediate Similarity	NPC472554
0.7789	Intermediate Similarity	NPC123252
0.7789	Intermediate Similarity	NPC219937
0.7789	Intermediate Similarity	NPC194485
0.7789	Intermediate Similarity	NPC153853
0.7789	Intermediate Similarity	NPC53890
0.7788	Intermediate Similarity	NPC154906
0.7755	Intermediate Similarity	NPC472995
0.7745	Intermediate Similarity	NPC473543
0.7732	Intermediate Similarity	NPC472416
0.7732	Intermediate Similarity	NPC472360
0.7727	Intermediate Similarity	NPC476719
0.7723	Intermediate Similarity	NPC472552
0.7708	Intermediate Similarity	NPC165180
0.77	Intermediate Similarity	NPC271295
0.77	Intermediate Similarity	NPC38855
0.77	Intermediate Similarity	NPC475877
0.7692	Intermediate Similarity	NPC477446
0.7692	Intermediate Similarity	NPC477447
0.7692	Intermediate Similarity	NPC470155
0.7684	Intermediate Similarity	NPC194642
0.7677	Intermediate Similarity	NPC120446
0.7677	Intermediate Similarity	NPC254121
0.767	Intermediate Similarity	NPC470980
0.7667	Intermediate Similarity	NPC472943
0.7667	Intermediate Similarity	NPC472951
0.766	Intermediate Similarity	NPC471377
0.7647	Intermediate Similarity	NPC473523
0.7647	Intermediate Similarity	NPC471467
0.7642	Intermediate Similarity	NPC157476
0.7634	Intermediate Similarity	NPC164424
0.7629	Intermediate Similarity	NPC119379
0.7624	Intermediate Similarity	NPC144486
0.7619	Intermediate Similarity	NPC305939
0.7609	Intermediate Similarity	NPC477978
0.7604	Intermediate Similarity	NPC191323
0.76	Intermediate Similarity	NPC469725
0.7596	Intermediate Similarity	NPC471205
0.7582	Intermediate Similarity	NPC470154
0.7582	Intermediate Similarity	NPC470156
0.7579	Intermediate Similarity	NPC160304
0.7576	Intermediate Similarity	NPC284518
0.7576	Intermediate Similarity	NPC475304
0.7576	Intermediate Similarity	NPC129569
0.7573	Intermediate Similarity	NPC283850
0.7553	Intermediate Similarity	NPC246347
0.7553	Intermediate Similarity	NPC279260
0.7551	Intermediate Similarity	NPC105375
0.7551	Intermediate Similarity	NPC476722
0.7551	Intermediate Similarity	NPC182826
0.7551	Intermediate Similarity	NPC3359
0.7549	Intermediate Similarity	NPC476471
0.7549	Intermediate Similarity	NPC109195
0.7549	Intermediate Similarity	NPC31085
0.7549	Intermediate Similarity	NPC475038
0.7549	Intermediate Similarity	NPC475344
0.7549	Intermediate Similarity	NPC165578
0.7547	Intermediate Similarity	NPC86217
0.7527	Intermediate Similarity	NPC299963
0.7526	Intermediate Similarity	NPC130840
0.7524	Intermediate Similarity	NPC181994
0.7524	Intermediate Similarity	NPC38948
0.75	Intermediate Similarity	NPC246028
0.75	Intermediate Similarity	NPC477126
0.75	Intermediate Similarity	NPC198549
0.75	Intermediate Similarity	NPC474395
0.75	Intermediate Similarity	NPC113976
0.75	Intermediate Similarity	NPC473963
0.75	Intermediate Similarity	NPC136781
0.75	Intermediate Similarity	NPC165405
0.7476	Intermediate Similarity	NPC474575
0.7476	Intermediate Similarity	NPC473694
0.7476	Intermediate Similarity	NPC99510
0.7476	Intermediate Similarity	NPC474124
0.7476	Intermediate Similarity	NPC475334
0.7476	Intermediate Similarity	NPC72842
0.7476	Intermediate Similarity	NPC475623
0.7475	Intermediate Similarity	NPC259042
0.7475	Intermediate Similarity	NPC157686
0.7475	Intermediate Similarity	NPC276110
0.7471	Intermediate Similarity	NPC476718
0.7453	Intermediate Similarity	NPC206618
0.7453	Intermediate Similarity	NPC475586
0.7453	Intermediate Similarity	NPC473570
0.7451	Intermediate Similarity	NPC235920
0.7451	Intermediate Similarity	NPC475617
0.7451	Intermediate Similarity	NPC475958
0.7451	Intermediate Similarity	NPC96784
0.7451	Intermediate Similarity	NPC308824
0.7449	Intermediate Similarity	NPC147272
0.7447	Intermediate Similarity	NPC93616
0.7447	Intermediate Similarity	NPC298595
0.7429	Intermediate Similarity	NPC470170
0.7429	Intermediate Similarity	NPC475781
0.7429	Intermediate Similarity	NPC470169
0.7426	Intermediate Similarity	NPC477876
0.7426	Intermediate Similarity	NPC300179
0.7426	Intermediate Similarity	NPC477875
0.7426	Intermediate Similarity	NPC102426
0.7423	Intermediate Similarity	NPC220216
0.7423	Intermediate Similarity	NPC48732
0.7423	Intermediate Similarity	NPC209816
0.7407	Intermediate Similarity	NPC473877
0.7404	Intermediate Similarity	NPC80809
0.7404	Intermediate Similarity	NPC201144
0.7404	Intermediate Similarity	NPC103298
0.7404	Intermediate Similarity	NPC288502
0.7404	Intermediate Similarity	NPC121518
0.7404	Intermediate Similarity	NPC181104
0.7404	Intermediate Similarity	NPC475335
0.7404	Intermediate Similarity	NPC475331
0.74	Intermediate Similarity	NPC103165
0.74	Intermediate Similarity	NPC256227
0.74	Intermediate Similarity	NPC471903
0.74	Intermediate Similarity	NPC473964
0.74	Intermediate Similarity	NPC210717
0.74	Intermediate Similarity	NPC93245
0.7396	Intermediate Similarity	NPC470872
0.7396	Intermediate Similarity	NPC473436
0.7383	Intermediate Similarity	NPC472214
0.7383	Intermediate Similarity	NPC156248
0.7383	Intermediate Similarity	NPC177047
0.7383	Intermediate Similarity	NPC472215
0.7383	Intermediate Similarity	NPC11491
0.7383	Intermediate Similarity	NPC140409

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 NPC91251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	2475
0.2-0.3	3879
0.3-0.4	1828
0.4-0.5	466
0.5-0.6	266
0.6-0.7	39
0.7-0.8	2
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
0.78	Intermediate Similarity	NPD5344	Discontinued
0.7525	Intermediate Similarity	NPD6648	Approved
0.6972	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3168	Discontinued
0.6768	Remote Similarity	NPD7524	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6733	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD46	Approved
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7516	Approved
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7638	Approved
0.6579	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6695	Phase 3
0.6471	Remote Similarity	NPD8380	Approved
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6471	Remote Similarity	NPD8033	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.641	Remote Similarity	NPD7115	Discovery
0.6396	Remote Similarity	NPD5357	Phase 1
0.6387	Remote Similarity	NPD8294	Approved
0.6387	Remote Similarity	NPD8377	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD371	Approved
0.6346	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD7983	Approved
0.6346	Remote Similarity	NPD7637	Suspended
0.6346	Remote Similarity	NPD8034	Phase 2
0.6286	Remote Similarity	NPD5779	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6283	Remote Similarity	NPD6686	Approved
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6275	Remote Similarity	NPD7750	Discontinued
0.6273	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6931	Approved
0.6224	Remote Similarity	NPD6930	Phase 2
0.6224	Remote Similarity	NPD7525	Registered
0.6207	Remote Similarity	NPD8297	Approved
0.6198	Remote Similarity	NPD8513	Phase 3
0.6198	Remote Similarity	NPD8515	Approved
0.6198	Remote Similarity	NPD8516	Approved
0.6198	Remote Similarity	NPD6921	Approved
0.6198	Remote Similarity	NPD8517	Approved
0.6198	Remote Similarity	NPD7503	Approved
0.6182	Remote Similarity	NPD1700	Approved
0.6176	Remote Similarity	NPD4249	Approved
0.6147	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6399	Phase 3
0.6129	Remote Similarity	NPD7507	Approved
0.6122	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6319	Approved
0.6111	Remote Similarity	NPD7319	Approved
0.6106	Remote Similarity	NPD7128	Approved
0.6106	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD5739	Approved
0.6106	Remote Similarity	NPD6402	Approved
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD6372	Approved
0.6061	Remote Similarity	NPD4819	Approved
0.6061	Remote Similarity	NPD4822	Approved
0.6061	Remote Similarity	NPD4821	Approved
0.6061	Remote Similarity	NPD4820	Approved
0.6061	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7492	Approved
0.604	Remote Similarity	NPD3669	Approved
0.604	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7087	Discontinued
0.6036	Remote Similarity	NPD4159	Approved
0.6034	Remote Similarity	NPD6371	Approved
0.6023	Remote Similarity	NPD1145	Discontinued
0.6017	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6899	Approved
0.5984	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD6650	Approved
0.5983	Remote Similarity	NPD6649	Approved
0.5968	Remote Similarity	NPD7604	Phase 2
0.596	Remote Similarity	NPD7645	Phase 2
0.5952	Remote Similarity	NPD8074	Phase 3
0.5952	Remote Similarity	NPD7078	Approved
0.5952	Remote Similarity	NPD8293	Discontinued
0.5932	Remote Similarity	NPD6882	Approved
0.5932	Remote Similarity	NPD6053	Discontinued
0.5926	Remote Similarity	NPD7748	Approved
0.5922	Remote Similarity	NPD6893	Approved
0.5922	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6925	Approved
0.5918	Remote Similarity	NPD5776	Phase 2
0.5913	Remote Similarity	NPD5697	Approved
0.5913	Remote Similarity	NPD5701	Approved
0.5913	Remote Similarity	NPD6412	Phase 2
0.5909	Remote Similarity	NPD7902	Approved
0.5906	Remote Similarity	NPD7736	Approved
0.59	Remote Similarity	NPD7332	Phase 2
0.59	Remote Similarity	NPD7514	Phase 3
0.5897	Remote Similarity	NPD7102	Approved
0.5897	Remote Similarity	NPD7290	Approved
0.5897	Remote Similarity	NPD6883	Approved
0.5888	Remote Similarity	NPD7515	Phase 2
0.5887	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD7154	Phase 3
0.5868	Remote Similarity	NPD6009	Approved
0.5859	Remote Similarity	NPD4271	Approved
0.5859	Remote Similarity	NPD4268	Approved
0.5859	Remote Similarity	NPD6118	Approved
0.5859	Remote Similarity	NPD6114	Approved
0.5859	Remote Similarity	NPD7145	Approved
0.5859	Remote Similarity	NPD6115	Approved
0.5859	Remote Similarity	NPD6697	Approved
0.5849	Remote Similarity	NPD1695	Approved
0.5849	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6101	Approved
0.5847	Remote Similarity	NPD6847	Approved
0.5847	Remote Similarity	NPD6617	Approved
0.5847	Remote Similarity	NPD6869	Approved
0.5847	Remote Similarity	NPD8130	Phase 1
0.5842	Remote Similarity	NPD6902	Approved
0.5842	Remote Similarity	NPD6898	Phase 1
0.584	Remote Similarity	NPD8328	Phase 3
0.5812	Remote Similarity	NPD6012	Approved
0.5812	Remote Similarity	NPD6013	Approved
0.5812	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6016	Approved
0.5806	Remote Similarity	NPD6015	Approved
0.5806	Remote Similarity	NPD5983	Phase 2
0.5773	Remote Similarity	NPD1810	Approved
0.5773	Remote Similarity	NPD1811	Approved
0.5766	Remote Similarity	NPD6083	Phase 2
0.5766	Remote Similarity	NPD6084	Phase 2
0.576	Remote Similarity	NPD5988	Approved
0.5758	Remote Similarity	NPD6116	Phase 1
0.5758	Remote Similarity	NPD6932	Approved
0.5748	Remote Similarity	NPD6336	Discontinued
0.5741	Remote Similarity	NPD6411	Approved
0.5728	Remote Similarity	NPD5362	Discontinued
0.5726	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD7339	Approved
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6942	Approved
0.5702	Remote Similarity	NPD5211	Phase 2
0.5701	Remote Similarity	NPD6051	Approved
0.5688	Remote Similarity	NPD8171	Discontinued
0.5684	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7839	Suspended
0.5673	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4786	Approved
0.5657	Remote Similarity	NPD6117	Approved
0.5657	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6933	Approved
0.5644	Remote Similarity	NPD6683	Phase 2
0.5636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7900	Approved
0.5636	Remote Similarity	NPD5282	Discontinued
0.5631	Remote Similarity	NPD3667	Approved
0.5631	Remote Similarity	NPD6435	Approved
0.5625	Remote Similarity	NPD4755	Approved
0.5619	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6924	Approved
0.5612	Remote Similarity	NPD6926	Approved
0.5604	Remote Similarity	NPD368	Approved
0.5603	Remote Similarity	NPD5141	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