NPASS Compound

Structure

CID161560 OpenBabel06191715532D 31 34 0 0 1 0 0 0 0 0999 V2000 -0.3660 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -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 -2.3660 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 1.3660 -2.3660 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 -1.3660 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 0.5000 -2.8660 0.0000 C 0 0 2 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 1.3660 -1.3660 0.0000 C 0 0 1 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 -1.3171 -2.6750 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 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 -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 23 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 11 28 1 0 0 0 0 13 17 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 26 2 0 0 0 0 15 31 1 0 0 0 0 16 12 1 6 0 0 0 16 20 1 0 0 0 0 17 27 1 6 0 0 0 18 9 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 1 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.25
Volume:	443.056
LogP:	2.995
LogD:	2.73
LogS:	-3.745
# Rotatable Bonds:	5
TPSA:	94.59
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	6.663
Fsp3:	0.833
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:	-4.857
MDCK Permeability:	6.484411278506741e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	55.003021240234375%
Volume Distribution (VD):	1.344
Pgp-substrate:	42.38261795043945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	4.604
Half-life (T1/2):	0.752

ADMET: Toxicity

hERG Blockers:	0.466
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.139
Carcinogencity:	0.227
Eye Corrosion:	0.007
Eye Irritation:	0.023
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC161560

Natural Product ID:	NPC161560
*Common Name:**	MRLKNBMAHKIZKS-PWLVGILOSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Klymollin D
Standard InCHIKey:	MRLKNBMAHKIZKS-PWLVGILOSA-N
Standard InCHI:	InChI=1S/C24H36O7/c1-12(2)16-10-19(29-14(4)25)24(11-28-24)21-18-9-13(3)17(27)7-8-23(6,31-15(5)26)22(30-18)20(16)21/h12,16-22,27H,3,7-11H2,1-2,4-6H3/t16-,17+,18-,19+,20-,21-,22-,23-,24+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H](C(C)C)[C@@H]2[C@H]([C@@]31CO3)[C@H]1CC(=C)[C@H](CC[C@@]([C@@H]2O1)(C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923038
PubChem CID:	56655500
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	=	25.1	%	PMID[468338]

☑ 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 NPC161560 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	196
0.1-0.2	1776
0.2-0.3	5739
0.3-0.4	14601
0.4-0.5	8698
0.5-0.6	7861
0.6-0.7	3509
0.7-0.8	281
0.8-0.85	15
0.85-0.9	6
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC91251
0.9643	High Similarity	NPC470260
0.9643	High Similarity	NPC75443
0.9639	High Similarity	NPC475684
0.9524	High Similarity	NPC44538
0.9412	High Similarity	NPC92370
0.9412	High Similarity	NPC476724
0.9412	High Similarity	NPC476723
0.9302	High Similarity	NPC291875
0.9286	High Similarity	NPC471379
0.9286	High Similarity	NPC196911
0.9277	High Similarity	NPC5958
0.9195	High Similarity	NPC312471
0.9195	High Similarity	NPC471378
0.9036	High Similarity	NPC77003
0.8876	High Similarity	NPC122057
0.8876	High Similarity	NPC312805
0.8837	High Similarity	NPC476725
0.8824	High Similarity	NPC127917
0.881	High Similarity	NPC118116
0.8605	High Similarity	NPC239308
0.8523	High Similarity	NPC321812
0.8523	High Similarity	NPC322922
0.8488	Intermediate Similarity	NPC103171
0.8462	Intermediate Similarity	NPC8729
0.8387	Intermediate Similarity	NPC476720
0.8256	Intermediate Similarity	NPC186594
0.8235	Intermediate Similarity	NPC264610
0.8229	Intermediate Similarity	NPC272223
0.8214	Intermediate Similarity	NPC136424
0.8214	Intermediate Similarity	NPC329626
0.8214	Intermediate Similarity	NPC293223
0.8211	Intermediate Similarity	NPC111348
0.8182	Intermediate Similarity	NPC470263
0.8132	Intermediate Similarity	NPC309656
0.8111	Intermediate Similarity	NPC214315
0.8095	Intermediate Similarity	NPC36479
0.8068	Intermediate Similarity	NPC216800
0.8065	Intermediate Similarity	NPC208839
0.8023	Intermediate Similarity	NPC191345
0.8023	Intermediate Similarity	NPC252483
0.8023	Intermediate Similarity	NPC43463
0.8021	Intermediate Similarity	NPC472998
0.8021	Intermediate Similarity	NPC473244
0.8	Intermediate Similarity	NPC241047
0.7957	Intermediate Similarity	NPC10274
0.7955	Intermediate Similarity	NPC211049
0.7917	Intermediate Similarity	NPC169270
0.7917	Intermediate Similarity	NPC306797
0.7917	Intermediate Similarity	NPC111834
0.7917	Intermediate Similarity	NPC292718
0.7907	Intermediate Similarity	NPC476719
0.7879	Intermediate Similarity	NPC470972
0.7872	Intermediate Similarity	NPC219516
0.7872	Intermediate Similarity	NPC165180
0.7841	Intermediate Similarity	NPC472951
0.7841	Intermediate Similarity	NPC472943
0.7816	Intermediate Similarity	NPC52755
0.7812	Intermediate Similarity	NPC469583
0.7802	Intermediate Similarity	NPC164424
0.7789	Intermediate Similarity	NPC26046
0.7778	Intermediate Similarity	NPC144486
0.7778	Intermediate Similarity	NPC98225
0.7767	Intermediate Similarity	NPC154906
0.7766	Intermediate Similarity	NPC123252
0.7766	Intermediate Similarity	NPC219937
0.7766	Intermediate Similarity	NPC191323
0.7766	Intermediate Similarity	NPC194485
0.7766	Intermediate Similarity	NPC153853
0.7766	Intermediate Similarity	NPC53890
0.7755	Intermediate Similarity	NPC469725
0.7753	Intermediate Similarity	NPC116320
0.7753	Intermediate Similarity	NPC119922
0.7742	Intermediate Similarity	NPC160304
0.7732	Intermediate Similarity	NPC221801
0.7732	Intermediate Similarity	NPC211810
0.7732	Intermediate Similarity	NPC472996
0.7732	Intermediate Similarity	NPC284194
0.7732	Intermediate Similarity	NPC472997
0.7732	Intermediate Similarity	NPC471765
0.7723	Intermediate Similarity	NPC473543
0.7717	Intermediate Similarity	NPC235196
0.7717	Intermediate Similarity	NPC228593
0.7708	Intermediate Similarity	NPC476722
0.7708	Intermediate Similarity	NPC472416
0.7708	Intermediate Similarity	NPC472360
0.77	Intermediate Similarity	NPC31085
0.7692	Intermediate Similarity	NPC299963
0.7684	Intermediate Similarity	NPC41838
0.7677	Intermediate Similarity	NPC188968
0.7677	Intermediate Similarity	NPC38855
0.7677	Intermediate Similarity	NPC79303
0.766	Intermediate Similarity	NPC194642
0.766	Intermediate Similarity	NPC246028
0.7653	Intermediate Similarity	NPC120446
0.7653	Intermediate Similarity	NPC274793
0.7647	Intermediate Similarity	NPC476718
0.7647	Intermediate Similarity	NPC470980
0.7629	Intermediate Similarity	NPC292178
0.7629	Intermediate Similarity	NPC86893
0.7624	Intermediate Similarity	NPC61442
0.7624	Intermediate Similarity	NPC471467
0.7624	Intermediate Similarity	NPC473523
0.7604	Intermediate Similarity	NPC147272
0.7604	Intermediate Similarity	NPC119379
0.76	Intermediate Similarity	NPC49532
0.76	Intermediate Similarity	NPC475617
0.76	Intermediate Similarity	NPC472554
0.7582	Intermediate Similarity	NPC477978
0.7579	Intermediate Similarity	NPC48732
0.7579	Intermediate Similarity	NPC220216
0.7551	Intermediate Similarity	NPC472995
0.7551	Intermediate Similarity	NPC284518
0.7551	Intermediate Similarity	NPC256227
0.7549	Intermediate Similarity	NPC283850
0.7527	Intermediate Similarity	NPC279260
0.7526	Intermediate Similarity	NPC476716
0.7526	Intermediate Similarity	NPC3359
0.7526	Intermediate Similarity	NPC39453
0.7526	Intermediate Similarity	NPC96736
0.7526	Intermediate Similarity	NPC178949
0.7525	Intermediate Similarity	NPC109195
0.7525	Intermediate Similarity	NPC476471
0.7525	Intermediate Similarity	NPC177701
0.7525	Intermediate Similarity	NPC475038
0.7525	Intermediate Similarity	NPC472552
0.7525	Intermediate Similarity	NPC475344
0.75	Intermediate Similarity	NPC124374
0.75	Intermediate Similarity	NPC473675
0.75	Intermediate Similarity	NPC271295
0.75	Intermediate Similarity	NPC38948
0.75	Intermediate Similarity	NPC475877
0.75	Intermediate Similarity	NPC102048
0.75	Intermediate Similarity	NPC130840
0.7476	Intermediate Similarity	NPC165405
0.7475	Intermediate Similarity	NPC473963
0.7475	Intermediate Similarity	NPC475033
0.7475	Intermediate Similarity	NPC198549
0.7475	Intermediate Similarity	NPC136781
0.7475	Intermediate Similarity	NPC113976
0.7475	Intermediate Similarity	NPC254121
0.7475	Intermediate Similarity	NPC475032
0.7474	Intermediate Similarity	NPC261320
0.7474	Intermediate Similarity	NPC128066
0.7473	Intermediate Similarity	NPC477446
0.7473	Intermediate Similarity	NPC470155
0.7473	Intermediate Similarity	NPC477447
0.7473	Intermediate Similarity	NPC472504
0.7453	Intermediate Similarity	NPC157476
0.7451	Intermediate Similarity	NPC475623
0.7451	Intermediate Similarity	NPC99510
0.7451	Intermediate Similarity	NPC473694
0.7451	Intermediate Similarity	NPC475334
0.7451	Intermediate Similarity	NPC72842
0.7451	Intermediate Similarity	NPC474124
0.7449	Intermediate Similarity	NPC157686
0.7449	Intermediate Similarity	NPC276110
0.7449	Intermediate Similarity	NPC259042
0.7447	Intermediate Similarity	NPC166857
0.7447	Intermediate Similarity	NPC471377
0.7429	Intermediate Similarity	NPC305939
0.7429	Intermediate Similarity	NPC206618
0.7426	Intermediate Similarity	NPC96784
0.7426	Intermediate Similarity	NPC308824
0.7426	Intermediate Similarity	NPC235920
0.7426	Intermediate Similarity	NPC475958
0.7423	Intermediate Similarity	NPC99653
0.7419	Intermediate Similarity	NPC476715
0.7419	Intermediate Similarity	NPC298595
0.7419	Intermediate Similarity	NPC93616
0.7404	Intermediate Similarity	NPC470170
0.7404	Intermediate Similarity	NPC470169
0.7404	Intermediate Similarity	NPC471205
0.74	Intermediate Similarity	NPC247233
0.74	Intermediate Similarity	NPC470067
0.74	Intermediate Similarity	NPC477875
0.74	Intermediate Similarity	NPC470066
0.74	Intermediate Similarity	NPC470068
0.74	Intermediate Similarity	NPC477876
0.74	Intermediate Similarity	NPC102426
0.74	Intermediate Similarity	NPC300179
0.7396	Intermediate Similarity	NPC209816
0.7379	Intermediate Similarity	NPC475331
0.7379	Intermediate Similarity	NPC475335
0.7379	Intermediate Similarity	NPC201144
0.7379	Intermediate Similarity	NPC121518
0.7379	Intermediate Similarity	NPC152966
0.7379	Intermediate Similarity	NPC80809
0.7379	Intermediate Similarity	NPC103298
0.7379	Intermediate Similarity	NPC288502
0.7379	Intermediate Similarity	NPC181104
0.7374	Intermediate Similarity	NPC93245
0.7374	Intermediate Similarity	NPC54248
0.7374	Intermediate Similarity	NPC57664
0.7374	Intermediate Similarity	NPC129569
0.7374	Intermediate Similarity	NPC103165
0.7374	Intermediate Similarity	NPC475304
0.7374	Intermediate Similarity	NPC473964
0.7374	Intermediate Similarity	NPC471903
0.7374	Intermediate Similarity	NPC276103

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 NPC161560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2398
0.2-0.3	3906
0.3-0.4	1876
0.4-0.5	462
0.5-0.6	279
0.6-0.7	38
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
0.7778	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD6648	Approved
0.6944	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4225	Approved
0.6869	Remote Similarity	NPD3168	Discontinued
0.6827	Remote Similarity	NPD7640	Approved
0.6827	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7524	Approved
0.6731	Remote Similarity	NPD7638	Approved
0.6727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7838	Discovery
0.67	Remote Similarity	NPD46	Approved
0.67	Remote Similarity	NPD6698	Approved
0.6697	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7516	Approved
0.6549	Remote Similarity	NPD8133	Approved
0.6542	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7115	Discovery
0.6495	Remote Similarity	NPD6695	Phase 3
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6466	Remote Similarity	NPD7327	Approved
0.6466	Remote Similarity	NPD7328	Approved
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8033	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.64	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD4250	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD5357	Phase 1
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8377	Approved
0.6356	Remote Similarity	NPD8294	Approved
0.6354	Remote Similarity	NPD7525	Registered
0.6339	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD371	Approved
0.6311	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD7983	Approved
0.6303	Remote Similarity	NPD8296	Approved
0.6303	Remote Similarity	NPD8380	Approved
0.6303	Remote Similarity	NPD8335	Approved
0.6303	Remote Similarity	NPD8379	Approved
0.6303	Remote Similarity	NPD8378	Approved
0.63	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6686	Approved
0.6238	Remote Similarity	NPD7750	Discontinued
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6186	Remote Similarity	NPD4822	Approved
0.6186	Remote Similarity	NPD6930	Phase 2
0.6186	Remote Similarity	NPD6931	Approved
0.6186	Remote Similarity	NPD4819	Approved
0.6186	Remote Similarity	NPD4821	Approved
0.6186	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4820	Approved
0.6174	Remote Similarity	NPD8297	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6167	Remote Similarity	NPD7503	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6163	Remote Similarity	NPD1145	Discontinued
0.6148	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD1700	Approved
0.614	Remote Similarity	NPD6371	Approved
0.6121	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6881	Approved
0.6106	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD7507	Approved
0.6098	Remote Similarity	NPD6616	Approved
0.6087	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6319	Approved
0.6083	Remote Similarity	NPD6059	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6082	Remote Similarity	NPD6929	Approved
0.6082	Remote Similarity	NPD7645	Phase 2
0.6066	Remote Similarity	NPD7604	Phase 2
0.6053	Remote Similarity	NPD6372	Approved
0.6053	Remote Similarity	NPD6373	Approved
0.6048	Remote Similarity	NPD7078	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7748	Approved
0.6034	Remote Similarity	NPD6053	Discontinued
0.6033	Remote Similarity	NPD6921	Approved
0.6019	Remote Similarity	NPD7902	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6018	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5697	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD4159	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5979	Remote Similarity	NPD6697	Approved
0.5979	Remote Similarity	NPD4268	Approved
0.5979	Remote Similarity	NPD6118	Approved
0.5979	Remote Similarity	NPD6114	Approved
0.5979	Remote Similarity	NPD6115	Approved
0.5979	Remote Similarity	NPD4271	Approved
0.5966	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6009	Approved
0.5962	Remote Similarity	NPD1695	Approved
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7319	Approved
0.5948	Remote Similarity	NPD6847	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD6649	Approved
0.5948	Remote Similarity	NPD6650	Approved
0.5948	Remote Similarity	NPD6617	Approved
0.5948	Remote Similarity	NPD6869	Approved
0.5922	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8074	Phase 3
0.5913	Remote Similarity	NPD6014	Approved
0.5913	Remote Similarity	NPD6013	Approved
0.5913	Remote Similarity	NPD6012	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD5983	Phase 2
0.5902	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5895	Remote Similarity	NPD1810	Approved
0.5895	Remote Similarity	NPD1811	Approved
0.5882	Remote Similarity	NPD6893	Approved
0.5876	Remote Similarity	NPD5776	Phase 2
0.5876	Remote Similarity	NPD6116	Phase 1
0.5876	Remote Similarity	NPD6925	Approved
0.5872	Remote Similarity	NPD6083	Phase 2
0.5872	Remote Similarity	NPD6084	Phase 2
0.5859	Remote Similarity	NPD7332	Phase 2
0.5859	Remote Similarity	NPD7514	Phase 3
0.5854	Remote Similarity	NPD5988	Approved
0.5849	Remote Similarity	NPD6411	Approved
0.5842	Remote Similarity	NPD5362	Discontinued
0.584	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD7339	Approved
0.5833	Remote Similarity	NPD6942	Approved
0.5826	Remote Similarity	NPD6011	Approved
0.5816	Remote Similarity	NPD7145	Approved
0.5812	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6051	Approved
0.5806	Remote Similarity	NPD8328	Phase 3
0.5806	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5211	Phase 2
0.58	Remote Similarity	NPD6898	Phase 1
0.58	Remote Similarity	NPD6902	Approved
0.5784	Remote Similarity	NPD4786	Approved
0.5784	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6933	Approved
0.5773	Remote Similarity	NPD6117	Approved
0.5743	Remote Similarity	NPD3667	Approved
0.5743	Remote Similarity	NPD6435	Approved
0.5741	Remote Similarity	NPD7900	Approved
0.5741	Remote Similarity	NPD5282	Discontinued
0.5741	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.573	Remote Similarity	NPD368	Approved
0.5729	Remote Similarity	NPD6926	Approved
0.5729	Remote Similarity	NPD6924	Approved
0.5728	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4755	Approved
0.5714	Remote Similarity	NPD6932	Approved
0.5702	Remote Similarity	NPD5141	Approved
0.57	Remote Similarity	NPD6928	Phase 2
0.57	Remote Similarity	NPD7509	Discontinued
0.5688	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5695	Phase 3
0.5686	Remote Similarity	NPD5332	Approved
0.5686	Remote Similarity	NPD5331	Approved
0.568	Remote Similarity	NPD6067	Discontinued
0.5673	Remote Similarity	NPD3618	Phase 1
0.567	Remote Similarity	NPD8264	Approved
0.566	Remote Similarity	NPD5328	Approved
0.5648	Remote Similarity	NPD8171	Discontinued
0.5648	Remote Similarity	NPD4202	Approved
0.5644	Remote Similarity	NPD4790	Discontinued
0.5644	Remote Similarity	NPD5369	Approved
0.5636	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD4696	Approved
0.5625	Remote Similarity	NPD5285	Approved
0.5625	Remote Similarity	NPD6033	Approved
0.5625	Remote Similarity	NPD5286	Approved
0.5625	Remote Similarity	NPD4700	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