NPASS Compound

Structure

NPC295478 OpenBabel07101718282D 31 33 0 0 1 0 0 0 0 0999 V2000 -3.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 -3.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3338 -3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 -3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 -2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -0.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 1.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6939 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5326 0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 1.9173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 -0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 16 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 14 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 1 1 1 0 0 0 14 22 1 0 0 0 0 15 2 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 4 1 6 0 0 0 17 22 1 0 0 0 0 17 27 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 6 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 6 0 0 0 22 28 1 1 0 0 0 23 29 1 1 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.25
Volume:	454.416
LogP:	2.569
LogD:	2.635
LogS:	-3.82
# Rotatable Bonds:	7
TPSA:	110.02
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.976
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.342
MDCK Permeability:	0.00015747081488370895
Pgp-inhibitor:	0.0
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.15
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	82.67382049560547%
Volume Distribution (VD):	1.664
Pgp-substrate:	11.130404472351074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.667
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	4.098
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.282
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.784
Skin Sensitization:	0.124
Carcinogencity:	0.71
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC295478

Natural Product ID:	NPC295478
*Common Name:**	Cytochalasin Z10
IUPAC Name:	(3S,3aS,4S,6S,7S,7aS)-3-benzyl-7-[(E,4S,5R,6R)-5,6-dihydroxy-4-methylhept-1-enyl]-6,7a-dihydroxy-4-methyl-5-methylidene-2,3,3a,4,6,7-hexahydroisoindol-1-one
Synonyms:	Cytochalasin Z10
Standard InCHIKey:	PQJSBGAESXRXQB-JGWJXVBRSA-N
Standard InCHI:	InChI=1S/C25H35NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14-15,17,19-23,27-29,31H,3,9,13H2,1-2,4H3,(H,26,30)/b12-8+/t14-,15+,17+,19-,20-,21-,22+,23+,25+/m0/s1
SMILES:	C[C@H]([C@@H]([C@H](C/C=C/[C@H]1[C@H](O)C(=C)[C@H]([C@@H]2[C@@]1(O)C(=N[C@H]2Cc1ccccc1)O)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459866
PubChem CID:	24970399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16792402]
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18507474]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	100000.0	nM	PMID[486015]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9600.0	nM	PMID[486015]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	69000.0	nM	PMID[486015]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000.0	nM	PMID[486015]

☑ 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 NPC295478 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	148
0.1-0.2	899
0.2-0.3	2128
0.3-0.4	8348
0.4-0.5	21143
0.5-0.6	9227
0.6-0.7	748
0.7-0.8	31
0.8-0.85	15
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9508	High Similarity	NPC278097
0.9449	High Similarity	NPC175870
0.8992	High Similarity	NPC228511
0.8923	High Similarity	NPC113325
0.8923	High Similarity	NPC279045
0.8889	High Similarity	NPC31171
0.8889	High Similarity	NPC237240
0.8696	High Similarity	NPC201692
0.8692	High Similarity	NPC42423
0.8593	High Similarity	NPC108852
0.8593	High Similarity	NPC261709
0.8593	High Similarity	NPC111586
0.8561	High Similarity	NPC90693
0.8561	High Similarity	NPC64897
0.8551	High Similarity	NPC173934
0.844	Intermediate Similarity	NPC4108
0.8406	Intermediate Similarity	NPC49565
0.8372	Intermediate Similarity	NPC472414
0.8321	Intermediate Similarity	NPC71271
0.8248	Intermediate Similarity	NPC239770
0.8163	Intermediate Similarity	NPC156348
0.8143	Intermediate Similarity	NPC262216
0.7939	Intermediate Similarity	NPC472415
0.7881	Intermediate Similarity	NPC15506
0.7794	Intermediate Similarity	NPC183722
0.777	Intermediate Similarity	NPC208725
0.7643	Intermediate Similarity	NPC477115
0.7518	Intermediate Similarity	NPC472413
0.7419	Intermediate Similarity	NPC194390
0.7419	Intermediate Similarity	NPC113326
0.7419	Intermediate Similarity	NPC224610
0.7419	Intermediate Similarity	NPC88267
0.7391	Intermediate Similarity	NPC116057
0.7287	Intermediate Similarity	NPC111108
0.7273	Intermediate Similarity	NPC64205
0.7255	Intermediate Similarity	NPC217801
0.7176	Intermediate Similarity	NPC474544
0.7176	Intermediate Similarity	NPC1986
0.7133	Intermediate Similarity	NPC132847
0.7068	Intermediate Similarity	NPC188010
0.7059	Intermediate Similarity	NPC275839
0.7051	Intermediate Similarity	NPC235460
0.7049	Intermediate Similarity	NPC58674
0.704	Intermediate Similarity	NPC266343
0.7015	Intermediate Similarity	NPC472862
0.7012	Intermediate Similarity	NPC203005
0.7	Intermediate Similarity	NPC44649
0.6953	Remote Similarity	NPC211551
0.6944	Remote Similarity	NPC3202
0.6923	Remote Similarity	NPC477157
0.6923	Remote Similarity	NPC477156
0.6912	Remote Similarity	NPC314992
0.6906	Remote Similarity	NPC35996
0.6906	Remote Similarity	NPC473870
0.6906	Remote Similarity	NPC473871
0.6905	Remote Similarity	NPC469457
0.6889	Remote Similarity	NPC2265
0.6887	Remote Similarity	NPC328824
0.686	Remote Similarity	NPC316108
0.6855	Remote Similarity	NPC25565
0.6835	Remote Similarity	NPC473889
0.6824	Remote Similarity	NPC322526
0.6818	Remote Similarity	NPC476744
0.6812	Remote Similarity	NPC190663
0.6809	Remote Similarity	NPC47667
0.68	Remote Similarity	NPC475439
0.68	Remote Similarity	NPC473501
0.6797	Remote Similarity	NPC94602
0.6797	Remote Similarity	NPC476757
0.6794	Remote Similarity	NPC64642
0.6794	Remote Similarity	NPC472982
0.6794	Remote Similarity	NPC149455
0.6786	Remote Similarity	NPC108286
0.6783	Remote Similarity	NPC259098
0.6783	Remote Similarity	NPC40488
0.6783	Remote Similarity	NPC197680
0.6781	Remote Similarity	NPC477680
0.6761	Remote Similarity	NPC475933
0.6761	Remote Similarity	NPC470158
0.6757	Remote Similarity	NPC473052
0.6757	Remote Similarity	NPC473055
0.6753	Remote Similarity	NPC476743
0.6742	Remote Similarity	NPC65855
0.6742	Remote Similarity	NPC292758
0.6726	Remote Similarity	NPC475345
0.6718	Remote Similarity	NPC472980
0.6718	Remote Similarity	NPC472979
0.6718	Remote Similarity	NPC27252
0.6714	Remote Similarity	NPC160493
0.6713	Remote Similarity	NPC476971
0.6713	Remote Similarity	NPC476972
0.6711	Remote Similarity	NPC472103
0.6711	Remote Similarity	NPC471201
0.6691	Remote Similarity	NPC477061
0.6691	Remote Similarity	NPC478015
0.6691	Remote Similarity	NPC45777
0.6691	Remote Similarity	NPC478014
0.6691	Remote Similarity	NPC478016
0.669	Remote Similarity	NPC477248
0.669	Remote Similarity	NPC477249
0.6688	Remote Similarity	NPC476741
0.6686	Remote Similarity	NPC475649
0.6667	Remote Similarity	NPC477839
0.6667	Remote Similarity	NPC58061
0.6667	Remote Similarity	NPC475578
0.6667	Remote Similarity	NPC237420
0.6667	Remote Similarity	NPC260194
0.6646	Remote Similarity	NPC257354
0.6643	Remote Similarity	NPC45821
0.6643	Remote Similarity	NPC476970
0.664	Remote Similarity	NPC303045
0.664	Remote Similarity	NPC161972
0.6627	Remote Similarity	NPC278272
0.6627	Remote Similarity	NPC120667
0.6625	Remote Similarity	NPC291359
0.6624	Remote Similarity	NPC476742
0.6623	Remote Similarity	NPC472100
0.6623	Remote Similarity	NPC313414
0.6621	Remote Similarity	NPC93632
0.6618	Remote Similarity	NPC473869
0.6607	Remote Similarity	NPC476113
0.6606	Remote Similarity	NPC304846
0.6603	Remote Similarity	NPC470274
0.6599	Remote Similarity	NPC328070
0.6596	Remote Similarity	NPC109151
0.6596	Remote Similarity	NPC252878
0.6585	Remote Similarity	NPC54125
0.6585	Remote Similarity	NPC89199
0.6584	Remote Similarity	NPC206736
0.6584	Remote Similarity	NPC195766
0.6573	Remote Similarity	NPC471758
0.6571	Remote Similarity	NPC80150
0.6571	Remote Similarity	NPC223451
0.6569	Remote Similarity	NPC317254
0.6567	Remote Similarity	NPC474149
0.6565	Remote Similarity	NPC243601
0.655	Remote Similarity	NPC474607
0.6549	Remote Similarity	NPC46427
0.6547	Remote Similarity	NPC310467
0.6547	Remote Similarity	NPC473860
0.6543	Remote Similarity	NPC329837
0.6541	Remote Similarity	NPC275027
0.6535	Remote Similarity	NPC311242
0.6535	Remote Similarity	NPC324602
0.6525	Remote Similarity	NPC284078
0.6524	Remote Similarity	NPC19555
0.6522	Remote Similarity	NPC476194
0.6522	Remote Similarity	NPC470820
0.6519	Remote Similarity	NPC184161
0.6513	Remote Similarity	NPC168861
0.6512	Remote Similarity	NPC474650
0.6512	Remote Similarity	NPC228400
0.6512	Remote Similarity	NPC214200
0.6503	Remote Similarity	NPC472373
0.6503	Remote Similarity	NPC307020
0.6503	Remote Similarity	NPC77691
0.65	Remote Similarity	NPC268572
0.65	Remote Similarity	NPC10730
0.65	Remote Similarity	NPC151197
0.65	Remote Similarity	NPC10875
0.6496	Remote Similarity	NPC12656
0.6496	Remote Similarity	NPC473137
0.6494	Remote Similarity	NPC327699
0.6489	Remote Similarity	NPC56168
0.6488	Remote Similarity	NPC88378
0.6488	Remote Similarity	NPC211713
0.6488	Remote Similarity	NPC231371
0.6486	Remote Similarity	NPC476976
0.6481	Remote Similarity	NPC477158
0.6479	Remote Similarity	NPC475328
0.6479	Remote Similarity	NPC475166
0.6475	Remote Similarity	NPC169328
0.6475	Remote Similarity	NPC84129
0.6474	Remote Similarity	NPC146097
0.6474	Remote Similarity	NPC227905
0.6474	Remote Similarity	NPC339338
0.6471	Remote Similarity	NPC475128
0.6471	Remote Similarity	NPC477155
0.6467	Remote Similarity	NPC478140
0.6458	Remote Similarity	NPC284022
0.6456	Remote Similarity	NPC472761
0.6454	Remote Similarity	NPC476990
0.6452	Remote Similarity	NPC471307
0.6452	Remote Similarity	NPC74936
0.6452	Remote Similarity	NPC141139
0.6452	Remote Similarity	NPC209764
0.6452	Remote Similarity	NPC78041
0.6452	Remote Similarity	NPC172128
0.6452	Remote Similarity	NPC159178
0.6452	Remote Similarity	NPC121872
0.6452	Remote Similarity	NPC116519
0.645	Remote Similarity	NPC110374
0.645	Remote Similarity	NPC474051
0.645	Remote Similarity	NPC289743
0.6449	Remote Similarity	NPC474486
0.6447	Remote Similarity	NPC197921
0.6447	Remote Similarity	NPC150712
0.6447	Remote Similarity	NPC243162
0.6446	Remote Similarity	NPC68328
0.6444	Remote Similarity	NPC133308

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 NPC295478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	507
0.2-0.3	770
0.3-0.4	2512
0.4-0.5	3448
0.5-0.6	1526
0.6-0.7	258
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7274	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6406	Approved
0.7218	Intermediate Similarity	NPD7522	Discontinued
0.704	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2238	Phase 2
0.6912	Remote Similarity	NPD2217	Approved
0.6912	Remote Similarity	NPD2218	Phase 2
0.6911	Remote Similarity	NPD4814	Discontinued
0.685	Remote Similarity	NPD4719	Phase 2
0.6809	Remote Similarity	NPD6325	Discontinued
0.6788	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5981	Approved
0.6719	Remote Similarity	NPD4818	Approved
0.6719	Remote Similarity	NPD4817	Approved
0.6708	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD3644	Approved
0.6692	Remote Similarity	NPD3642	Approved
0.6692	Remote Similarity	NPD3643	Approved
0.6691	Remote Similarity	NPD7725	Approved
0.669	Remote Similarity	NPD4738	Phase 2
0.6643	Remote Similarity	NPD4103	Phase 2
0.6643	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1710	Approved
0.6615	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6690	Approved
0.6596	Remote Similarity	NPD3529	Phase 2
0.6596	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2568	Approved
0.6569	Remote Similarity	NPD7508	Discontinued
0.6565	Remote Similarity	NPD5717	Approved
0.6547	Remote Similarity	NPD7741	Discontinued
0.6544	Remote Similarity	NPD2234	Approved
0.6544	Remote Similarity	NPD2229	Approved
0.6544	Remote Similarity	NPD2228	Approved
0.6538	Remote Similarity	NPD3680	Approved
0.6538	Remote Similarity	NPD3682	Approved
0.6535	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3552	Approved
0.6533	Remote Similarity	NPD3555	Approved
0.6533	Remote Similarity	NPD3553	Approved
0.6533	Remote Similarity	NPD3554	Approved
0.6531	Remote Similarity	NPD7908	Discontinued
0.6522	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4659	Approved
0.6503	Remote Similarity	NPD9622	Approved
0.65	Remote Similarity	NPD6072	Discontinued
0.6497	Remote Similarity	NPD7526	Approved
0.6497	Remote Similarity	NPD52	Approved
0.6497	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3400	Discontinued
0.6494	Remote Similarity	NPD6676	Phase 2
0.6479	Remote Similarity	NPD5618	Discontinued
0.6479	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4005	Discontinued
0.6475	Remote Similarity	NPD6360	Discontinued
0.6462	Remote Similarity	NPD855	Approved
0.6462	Remote Similarity	NPD854	Approved
0.6457	Remote Similarity	NPD2895	Discontinued
0.6454	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5035	Approved
0.6447	Remote Similarity	NPD2161	Phase 2
0.6444	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD2233	Approved
0.6434	Remote Similarity	NPD2232	Approved
0.6434	Remote Similarity	NPD2230	Approved
0.6429	Remote Similarity	NPD3718	Approved
0.6429	Remote Similarity	NPD4479	Discontinued
0.6429	Remote Similarity	NPD3719	Approved
0.6423	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5773	Approved
0.642	Remote Similarity	NPD5772	Approved
0.6414	Remote Similarity	NPD3094	Phase 2
0.6412	Remote Similarity	NPD3683	Approved
0.6412	Remote Similarity	NPD4231	Approved
0.6412	Remote Similarity	NPD4229	Approved
0.6412	Remote Similarity	NPD3681	Approved
0.6412	Remote Similarity	NPD1542	Approved
0.6408	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2613	Approved
0.6379	Remote Similarity	NPD5036	Approved
0.6377	Remote Similarity	NPD9614	Approved
0.6377	Remote Similarity	NPD9618	Approved
0.6376	Remote Similarity	NPD6405	Approved
0.6376	Remote Similarity	NPD6407	Approved
0.6376	Remote Similarity	NPD1136	Approved
0.6376	Remote Similarity	NPD1132	Approved
0.6376	Remote Similarity	NPD1130	Approved
0.6376	Remote Similarity	NPD8118	Discontinued
0.637	Remote Similarity	NPD2195	Approved
0.637	Remote Similarity	NPD2194	Approved
0.6358	Remote Similarity	NPD817	Approved
0.6358	Remote Similarity	NPD5314	Approved
0.6358	Remote Similarity	NPD823	Approved
0.6357	Remote Similarity	NPD9612	Approved
0.6357	Remote Similarity	NPD9609	Approved
0.6357	Remote Similarity	NPD9611	Approved
0.6353	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5038	Approved
0.6343	Remote Similarity	NPD5037	Approved
0.6338	Remote Similarity	NPD5126	Approved
0.6338	Remote Similarity	NPD5125	Phase 3
0.6338	Remote Similarity	NPD7342	Discontinued
0.6336	Remote Similarity	NPD5716	Approved
0.6336	Remote Similarity	NPD4119	Approved
0.6336	Remote Similarity	NPD1540	Approved
0.6333	Remote Similarity	NPD8265	Approved
0.6333	Remote Similarity	NPD3062	Approved
0.6333	Remote Similarity	NPD3061	Approved
0.6333	Remote Similarity	NPD3059	Approved
0.6331	Remote Similarity	NPD4031	Approved
0.6331	Remote Similarity	NPD4032	Approved
0.6324	Remote Similarity	NPD4254	Approved
0.6324	Remote Similarity	NPD4253	Approved
0.6323	Remote Similarity	NPD3638	Discontinued
0.6319	Remote Similarity	NPD2561	Approved
0.6319	Remote Similarity	NPD2562	Approved
0.6312	Remote Similarity	NPD5303	Approved
0.6312	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5304	Approved
0.6312	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2969	Approved
0.631	Remote Similarity	NPD2970	Approved
0.6309	Remote Similarity	NPD601	Approved
0.6309	Remote Similarity	NPD597	Approved
0.6309	Remote Similarity	NPD598	Approved
0.6309	Remote Similarity	NPD8011	Discontinued
0.6301	Remote Similarity	NPD2579	Approved
0.6299	Remote Similarity	NPD4725	Approved
0.6299	Remote Similarity	NPD4721	Approved
0.6299	Remote Similarity	NPD4726	Approved
0.6296	Remote Similarity	NPD4717	Approved
0.6296	Remote Similarity	NPD4720	Approved
0.6296	Remote Similarity	NPD4718	Approved
0.6288	Remote Similarity	NPD4656	Approved
0.6288	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD4658	Approved
0.6286	Remote Similarity	NPD3123	Discovery
0.6286	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2575	Approved
0.6282	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6331	Phase 2
0.6276	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD27	Approved
0.6272	Remote Similarity	NPD2489	Approved
0.6271	Remote Similarity	NPD8361	Approved
0.6271	Remote Similarity	NPD8360	Approved
0.6269	Remote Similarity	NPD5705	Approved
0.6269	Remote Similarity	NPD5706	Approved
0.6269	Remote Similarity	NPD5704	Approved
0.6268	Remote Similarity	NPD4093	Discontinued
0.6267	Remote Similarity	NPD2574	Discontinued
0.6267	Remote Similarity	NPD2566	Approved
0.6267	Remote Similarity	NPD7715	Approved
0.6267	Remote Similarity	NPD3090	Approved
0.6267	Remote Similarity	NPD3616	Approved
0.6267	Remote Similarity	NPD7714	Approved
0.6267	Remote Similarity	NPD3614	Approved
0.6267	Remote Similarity	NPD3087	Approved
0.6267	Remote Similarity	NPD2573	Approved
0.6267	Remote Similarity	NPD3615	Approved
0.6267	Remote Similarity	NPD4746	Phase 3
0.6267	Remote Similarity	NPD2570	Approved
0.6267	Remote Similarity	NPD839	Approved
0.6267	Remote Similarity	NPD2571	Approved
0.6267	Remote Similarity	NPD3088	Approved
0.6267	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD840	Approved
0.6267	Remote Similarity	NPD4745	Approved
0.6267	Remote Similarity	NPD3089	Approved
0.6264	Remote Similarity	NPD7312	Approved
0.6264	Remote Similarity	NPD7311	Approved
0.6264	Remote Similarity	NPD7310	Approved
0.6264	Remote Similarity	NPD7313	Approved
0.6259	Remote Similarity	NPD599	Approved
0.6259	Remote Similarity	NPD602	Approved
0.625	Remote Similarity	NPD1792	Phase 2
0.625	Remote Similarity	NPD2609	Approved
0.625	Remote Similarity	NPD4218	Approved
0.625	Remote Similarity	NPD3132	Approved
0.625	Remote Similarity	NPD4215	Approved
0.625	Remote Similarity	NPD2608	Approved
0.625	Remote Similarity	NPD4663	Approved
0.625	Remote Similarity	NPD8173	Phase 2
0.625	Remote Similarity	NPD4216	Approved
0.625	Remote Similarity	NPD2610	Approved
0.625	Remote Similarity	NPD8172	Phase 2
0.625	Remote Similarity	NPD3092	Approved
0.625	Remote Similarity	NPD3051	Approved
0.625	Remote Similarity	NPD3131	Approved
0.625	Remote Similarity	NPD2612	Approved
0.625	Remote Similarity	NPD2611	Approved
0.625	Remote Similarity	NPD4217	Approved
0.6243	Remote Similarity	NPD5030	Phase 2
0.6243	Remote Similarity	NPD8485	Approved
0.6242	Remote Similarity	NPD8323	Discontinued
0.6242	Remote Similarity	NPD3692	Discontinued

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