NPASS Compound

Structure

NPC71271 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.5050 -2.2043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -1.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 -3.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1428 0.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2624 -1.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4192 -1.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2624 -0.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1867 -3.2202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0605 -2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5760 -1.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4192 0.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2193 -3.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1296 0.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0890 0.1993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7327 0.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5633 -1.9568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4392 -2.0880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1384 -3.0140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5760 -0.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4656 -2.4929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8895 -0.3960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4122 -0.6251 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7877 -1.3644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1860 -3.2164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5355 -0.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6515 -0.7236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9859 -0.1797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1647 -1.5668 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 1.2554 0.3805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1149 -4.1425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4615 -0.6826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6199 -0.6218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8965 0.1649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 3 18 1 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 16 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 1 1 6 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 15 1 1 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 28 1 6 0 0 0 24 31 1 1 0 0 0 25 27 1 0 0 0 0 25 32 2 0 0 0 0 26 29 2 0 0 0 0 26 33 1 0 0 0 0 27 4 1 1 0 0 0 27 34 1 0 0 0 0 28 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	465.25
Volume:	492.474
LogP:	2.529
LogD:	2.485
LogS:	-3.177
# Rotatable Bonds:	2
TPSA:	106.86
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	5.8
Fsp3:	0.5
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:	-5.257
MDCK Permeability:	1.2232570952619426e-05
Pgp-inhibitor:	0.136
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.205
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	84.50293731689453%
Volume Distribution (VD):	0.924
Pgp-substrate:	4.783425331115723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.717
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.327
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	4.59
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.113
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.561

Download Data

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

Natural Product: NPC71271

Natural Product ID:	NPC71271
*Common Name:**	Deacetylcytochalasin C
IUPAC Name:	n.a.
Synonyms:	Deacetylcytochalasin C
Standard InCHIKey:	AOIKFORBJLUJGZ-NIOUNHJPSA-N
Standard InCHI:	InChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16,20-24,30-31,34H,9,15H2,1-4H3,(H,29,33)/b12-8+,14-13+/t16-,20-,21-,22+,23-,24+,27+,28+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@H]2[C@@H](C(=C(C)[C@H]3[C@H](Cc4ccccc4)N=C([C@@]23[C@@H](/C=C/[C@](C)(C1=O)O)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519782
PubChem CID:	21668730
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans

*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
NPO9967	Metarhizium anisopliae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650095]
NPO9967	Metarhizium anisopliae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18044842]
NPO9967	Metarhizium anisopliae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20233596]
NPO33244	crodyceps taii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25863432]
NPO9967	Metarhizium anisopliae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623030]
NPO9967	Metarhizium anisopliae	Species	Clavicipitaceae	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
IC50	4
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13620.0	nM	PMID[548097]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	200000.0	nM	PMID[548097]
NPT118	Organism	Oryza sativa	Oryza sativa	Activity	=	83.0	%	PMID[548096]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3670.0	nM	PMID[548097]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31080.0	nM	PMID[548097]

☑ 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 NPC71271 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	103
0.1-0.2	643
0.2-0.3	2143
0.3-0.4	8443
0.4-0.5	23641
0.5-0.6	6792
0.6-0.7	841
0.7-0.8	66
0.8-0.85	11
0.85-0.9	7
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC472414
0.9597	High Similarity	NPC42423
0.9583	High Similarity	NPC472415
0.9291	High Similarity	NPC228511
0.9219	High Similarity	NPC279045
0.9219	High Similarity	NPC113325
0.9084	High Similarity	NPC239770
0.8906	High Similarity	NPC183722
0.8855	High Similarity	NPC175870
0.8855	High Similarity	NPC208725
0.875	High Similarity	NPC472413
0.874	High Similarity	NPC278097
0.8702	High Similarity	NPC64897
0.8702	High Similarity	NPC90693
0.8676	High Similarity	NPC262216
0.8676	High Similarity	NPC49565
0.8462	Intermediate Similarity	NPC116057
0.8321	Intermediate Similarity	NPC295478
0.8188	Intermediate Similarity	NPC111586
0.8188	Intermediate Similarity	NPC261709
0.8188	Intermediate Similarity	NPC108852
0.7931	Intermediate Similarity	NPC4108
0.7832	Intermediate Similarity	NPC31171
0.7832	Intermediate Similarity	NPC237240
0.7671	Intermediate Similarity	NPC201692
0.7597	Intermediate Similarity	NPC188010
0.7534	Intermediate Similarity	NPC173934
0.7444	Intermediate Similarity	NPC190663
0.7347	Intermediate Similarity	NPC328824
0.7333	Intermediate Similarity	NPC160493
0.7312	Intermediate Similarity	NPC477115
0.7308	Intermediate Similarity	NPC15506
0.7299	Intermediate Similarity	NPC477249
0.7299	Intermediate Similarity	NPC477248
0.728	Intermediate Similarity	NPC194390
0.728	Intermediate Similarity	NPC224610
0.728	Intermediate Similarity	NPC88267
0.728	Intermediate Similarity	NPC113326
0.7255	Intermediate Similarity	NPC217801
0.7248	Intermediate Similarity	NPC476757
0.723	Intermediate Similarity	NPC44649
0.7226	Intermediate Similarity	NPC156348
0.7185	Intermediate Similarity	NPC478016
0.7185	Intermediate Similarity	NPC478015
0.7185	Intermediate Similarity	NPC478014
0.7185	Intermediate Similarity	NPC80150
0.7183	Intermediate Similarity	NPC328070
0.7177	Intermediate Similarity	NPC469457
0.7172	Intermediate Similarity	NPC322526
0.7103	Intermediate Similarity	NPC473055
0.7103	Intermediate Similarity	NPC473052
0.7063	Intermediate Similarity	NPC3202
0.7055	Intermediate Similarity	NPC153007
0.7055	Intermediate Similarity	NPC471201
0.7051	Intermediate Similarity	NPC235460
0.705	Intermediate Similarity	NPC47667
0.7049	Intermediate Similarity	NPC58674
0.7037	Intermediate Similarity	NPC310467
0.7031	Intermediate Similarity	NPC191215
0.7031	Intermediate Similarity	NPC274089
0.7014	Intermediate Similarity	NPC477680
0.7014	Intermediate Similarity	NPC132847
0.7007	Intermediate Similarity	NPC150712
0.7	Intermediate Similarity	NPC475578
0.6963	Remote Similarity	NPC169328
0.6953	Remote Similarity	NPC211551
0.6934	Remote Similarity	NPC45777
0.6934	Remote Similarity	NPC477061
0.6917	Remote Similarity	NPC474544
0.6917	Remote Similarity	NPC1986
0.6867	Remote Similarity	NPC473922
0.686	Remote Similarity	NPC316108
0.6855	Remote Similarity	NPC25565
0.6849	Remote Similarity	NPC474787
0.6849	Remote Similarity	NPC9687
0.6849	Remote Similarity	NPC475318
0.6849	Remote Similarity	NPC49577
0.6849	Remote Similarity	NPC260045
0.6849	Remote Similarity	NPC273907
0.6849	Remote Similarity	NPC118099
0.6849	Remote Similarity	NPC90194
0.6849	Remote Similarity	NPC475598
0.6849	Remote Similarity	NPC79465
0.6849	Remote Similarity	NPC293377
0.6849	Remote Similarity	NPC76785
0.6849	Remote Similarity	NPC474811
0.6849	Remote Similarity	NPC474855
0.6849	Remote Similarity	NPC476102
0.6849	Remote Similarity	NPC151706
0.6842	Remote Similarity	NPC273814
0.6839	Remote Similarity	NPC275839
0.6835	Remote Similarity	NPC474862
0.6835	Remote Similarity	NPC109151
0.6835	Remote Similarity	NPC252878
0.6828	Remote Similarity	NPC313663
0.6818	Remote Similarity	NPC470274
0.6806	Remote Similarity	NPC49272
0.68	Remote Similarity	NPC475439
0.68	Remote Similarity	NPC473501
0.6797	Remote Similarity	NPC339338
0.6797	Remote Similarity	NPC227905
0.6797	Remote Similarity	NPC146097
0.6797	Remote Similarity	NPC471317
0.6797	Remote Similarity	NPC94602
0.6788	Remote Similarity	NPC211713
0.6788	Remote Similarity	NPC314992
0.6788	Remote Similarity	NPC88378
0.6788	Remote Similarity	NPC237420
0.6786	Remote Similarity	NPC6975
0.6786	Remote Similarity	NPC46427
0.6783	Remote Similarity	NPC40488
0.6779	Remote Similarity	NPC197921
0.6767	Remote Similarity	NPC471188
0.6767	Remote Similarity	NPC471189
0.6765	Remote Similarity	NPC2265
0.6763	Remote Similarity	NPC202521
0.675	Remote Similarity	NPC67080
0.6733	Remote Similarity	NPC91953
0.6718	Remote Similarity	NPC140251
0.6718	Remote Similarity	NPC472980
0.6718	Remote Similarity	NPC307903
0.671	Remote Similarity	NPC185404
0.6709	Remote Similarity	NPC93343
0.6707	Remote Similarity	NPC203005
0.6691	Remote Similarity	NPC476990
0.6689	Remote Similarity	NPC478140
0.6667	Remote Similarity	NPC202613
0.6667	Remote Similarity	NPC474563
0.6667	Remote Similarity	NPC35996
0.6645	Remote Similarity	NPC5620
0.6644	Remote Similarity	NPC246913
0.6643	Remote Similarity	NPC476281
0.6643	Remote Similarity	NPC470816
0.6643	Remote Similarity	NPC476184
0.6642	Remote Similarity	NPC105141
0.6642	Remote Similarity	NPC242764
0.6642	Remote Similarity	NPC470820
0.6641	Remote Similarity	NPC214200
0.6641	Remote Similarity	NPC228400
0.664	Remote Similarity	NPC303045
0.664	Remote Similarity	NPC161972
0.6627	Remote Similarity	NPC475345
0.6625	Remote Similarity	NPC476194
0.6623	Remote Similarity	NPC469360
0.6621	Remote Similarity	NPC478147
0.662	Remote Similarity	NPC77691
0.662	Remote Similarity	NPC473938
0.6618	Remote Similarity	NPC93181
0.6617	Remote Similarity	NPC292758
0.6617	Remote Similarity	NPC65855
0.6597	Remote Similarity	NPC319766
0.6596	Remote Similarity	NPC291027
0.6596	Remote Similarity	NPC475328
0.6596	Remote Similarity	NPC169485
0.6596	Remote Similarity	NPC213126
0.6596	Remote Similarity	NPC317474
0.6596	Remote Similarity	NPC84281
0.6594	Remote Similarity	NPC254088
0.6593	Remote Similarity	NPC477245
0.6593	Remote Similarity	NPC477246
0.6593	Remote Similarity	NPC474584
0.6591	Remote Similarity	NPC27252
0.6591	Remote Similarity	NPC472979
0.6588	Remote Similarity	NPC475649
0.6577	Remote Similarity	NPC64205
0.6573	Remote Similarity	NPC4974
0.6571	Remote Similarity	NPC476183
0.6569	Remote Similarity	NPC317254
0.6569	Remote Similarity	NPC9274
0.6567	Remote Similarity	NPC323007
0.6567	Remote Similarity	NPC477247
0.6567	Remote Similarity	NPC474149
0.6565	Remote Similarity	NPC471186
0.6564	Remote Similarity	NPC71205
0.6561	Remote Similarity	NPC472761
0.6558	Remote Similarity	NPC260194
0.6554	Remote Similarity	NPC248283
0.6554	Remote Similarity	NPC15850
0.6552	Remote Similarity	NPC469666
0.6552	Remote Similarity	NPC296712
0.6549	Remote Similarity	NPC273336
0.6549	Remote Similarity	NPC476278
0.6549	Remote Similarity	NPC182333
0.6543	Remote Similarity	NPC476750
0.6538	Remote Similarity	NPC19856
0.6536	Remote Similarity	NPC471680
0.6528	Remote Similarity	NPC65310
0.6527	Remote Similarity	NPC120667
0.6527	Remote Similarity	NPC278272
0.6525	Remote Similarity	NPC472981
0.6522	Remote Similarity	NPC472862
0.6522	Remote Similarity	NPC470544
0.6522	Remote Similarity	NPC212891
0.6515	Remote Similarity	NPC327481
0.6514	Remote Similarity	NPC317882
0.6514	Remote Similarity	NPC473300
0.6514	Remote Similarity	NPC471754
0.6514	Remote Similarity	NPC453583
0.6514	Remote Similarity	NPC475336
0.6513	Remote Similarity	NPC161069

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 NPC71271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	411
0.2-0.3	822
0.3-0.4	2277
0.4-0.5	3544
0.5-0.6	1688
0.6-0.7	300
0.7-0.8	5
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
0.7832	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6325	Discontinued
0.7381	Intermediate Similarity	NPD6406	Approved
0.7111	Intermediate Similarity	NPD5981	Approved
0.709	Intermediate Similarity	NPD7522	Discontinued
0.6984	Remote Similarity	NPD4719	Phase 2
0.6947	Remote Similarity	NPD3643	Approved
0.6947	Remote Similarity	NPD3642	Approved
0.6947	Remote Similarity	NPD3644	Approved
0.6911	Remote Similarity	NPD4814	Discontinued
0.6905	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3123	Discovery
0.6828	Remote Similarity	NPD7715	Approved
0.6828	Remote Similarity	NPD7714	Approved
0.6812	Remote Similarity	NPD7725	Approved
0.6788	Remote Similarity	NPD2218	Phase 2
0.6788	Remote Similarity	NPD2217	Approved
0.6781	Remote Similarity	NPD8265	Approved
0.6744	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5618	Discontinued
0.6692	Remote Similarity	NPD5717	Approved
0.669	Remote Similarity	NPD4738	Phase 2
0.669	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4479	Discontinued
0.6643	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5704	Approved
0.6641	Remote Similarity	NPD5706	Approved
0.6641	Remote Similarity	NPD5705	Approved
0.6613	Remote Similarity	NPD6690	Approved
0.6601	Remote Similarity	NPD6676	Phase 2
0.6596	Remote Similarity	NPD3132	Approved
0.6596	Remote Similarity	NPD2611	Approved
0.6596	Remote Similarity	NPD2610	Approved
0.6596	Remote Similarity	NPD4216	Approved
0.6596	Remote Similarity	NPD2608	Approved
0.6596	Remote Similarity	NPD4217	Approved
0.6596	Remote Similarity	NPD3131	Approved
0.6596	Remote Similarity	NPD4218	Approved
0.6596	Remote Similarity	NPD2609	Approved
0.6596	Remote Similarity	NPD2612	Approved
0.6596	Remote Similarity	NPD4215	Approved
0.6596	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD854	Approved
0.6589	Remote Similarity	NPD4818	Approved
0.6589	Remote Similarity	NPD4817	Approved
0.6589	Remote Similarity	NPD855	Approved
0.6577	Remote Similarity	NPD8173	Phase 2
0.6577	Remote Similarity	NPD8172	Phase 2
0.6575	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7342	Discontinued
0.6565	Remote Similarity	NPD999	Phase 2
0.6565	Remote Similarity	NPD1018	Approved
0.6556	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7084	Phase 3
0.6538	Remote Similarity	NPD6647	Phase 2
0.6531	Remote Similarity	NPD4621	Approved
0.6531	Remote Similarity	NPD4619	Approved
0.6528	Remote Similarity	NPD2160	Approved
0.6528	Remote Similarity	NPD2628	Approved
0.6528	Remote Similarity	NPD2625	Approved
0.6528	Remote Similarity	NPD2626	Approved
0.6528	Remote Similarity	NPD2627	Approved
0.6528	Remote Similarity	NPD2159	Approved
0.6522	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7978	Discontinued
0.651	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2613	Approved
0.6503	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5159	Phase 2
0.6503	Remote Similarity	NPD5157	Phase 1
0.65	Remote Similarity	NPD1710	Approved
0.6497	Remote Similarity	NPD7613	Discontinued
0.6494	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3400	Discontinued
0.6494	Remote Similarity	NPD2575	Approved
0.6486	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8118	Discontinued
0.6484	Remote Similarity	NPD9609	Approved
0.6484	Remote Similarity	NPD9611	Approved
0.6484	Remote Similarity	NPD9612	Approved
0.648	Remote Similarity	NPD752	Approved
0.6479	Remote Similarity	NPD4807	Approved
0.6479	Remote Similarity	NPD4806	Approved
0.6479	Remote Similarity	NPD3529	Phase 2
0.6474	Remote Similarity	NPD5036	Approved
0.6471	Remote Similarity	NPD2607	Approved
0.6466	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5716	Approved
0.6462	Remote Similarity	NPD4119	Approved
0.6454	Remote Similarity	NPD5305	Approved
0.6454	Remote Similarity	NPD5306	Approved
0.6452	Remote Similarity	NPD8323	Discontinued
0.6449	Remote Similarity	NPD7508	Discontinued
0.6444	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD8416	Discontinued
0.6437	Remote Similarity	NPD5038	Approved
0.6437	Remote Similarity	NPD5037	Approved
0.6433	Remote Similarity	NPD5030	Phase 2
0.6429	Remote Similarity	NPD719	Approved
0.6429	Remote Similarity	NPD720	Approved
0.6412	Remote Similarity	NPD3682	Approved
0.6412	Remote Similarity	NPD3683	Approved
0.6412	Remote Similarity	NPD3681	Approved
0.6412	Remote Similarity	NPD3680	Approved
0.6406	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4955	Approved
0.6395	Remote Similarity	NPD5201	Approved
0.6395	Remote Similarity	NPD4954	Approved
0.6395	Remote Similarity	NPD4617	Approved
0.6395	Remote Similarity	NPD5028	Approved
0.6395	Remote Similarity	NPD5026	Approved
0.6395	Remote Similarity	NPD36	Approved
0.6395	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5203	Approved
0.6395	Remote Similarity	NPD4620	Approved
0.6395	Remote Similarity	NPD5034	Approved
0.6383	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1711	Phase 2
0.6377	Remote Similarity	NPD2629	Approved
0.6376	Remote Similarity	NPD2566	Approved
0.6376	Remote Similarity	NPD3088	Approved
0.6376	Remote Similarity	NPD3087	Approved
0.6376	Remote Similarity	NPD3090	Approved
0.6376	Remote Similarity	NPD3614	Approved
0.6376	Remote Similarity	NPD2573	Approved
0.6376	Remote Similarity	NPD3615	Approved
0.6376	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3616	Approved
0.6376	Remote Similarity	NPD2570	Approved
0.6376	Remote Similarity	NPD4746	Phase 3
0.6376	Remote Similarity	NPD2574	Discontinued
0.6376	Remote Similarity	NPD3089	Approved
0.6376	Remote Similarity	NPD4745	Approved
0.6376	Remote Similarity	NPD2571	Approved
0.6364	Remote Similarity	NPD8361	Approved
0.6364	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD10	Approved
0.6364	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD311	Approved
0.6364	Remote Similarity	NPD315	Approved
0.6364	Remote Similarity	NPD8360	Approved
0.6364	Remote Similarity	NPD310	Approved
0.6364	Remote Similarity	NPD314	Approved
0.6364	Remote Similarity	NPD309	Approved
0.6358	Remote Similarity	NPD5035	Approved
0.6358	Remote Similarity	NPD7011	Discontinued
0.6357	Remote Similarity	NPD1758	Phase 1
0.6353	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7295	Approved
0.6343	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD8417	Discontinued
0.6333	Remote Similarity	NPD5120	Approved
0.6333	Remote Similarity	NPD8485	Approved
0.6333	Remote Similarity	NPD5121	Approved
0.6333	Remote Similarity	NPD6309	Approved
0.6333	Remote Similarity	NPD5119	Approved
0.6333	Remote Similarity	NPD6311	Approved
0.6333	Remote Similarity	NPD6310	Approved
0.6331	Remote Similarity	NPD4031	Approved
0.6331	Remote Similarity	NPD1348	Approved
0.6331	Remote Similarity	NPD4032	Approved
0.6328	Remote Similarity	NPD2895	Discontinued
0.6327	Remote Similarity	NPD5204	Approved
0.6327	Remote Similarity	NPD3661	Approved
0.6327	Remote Similarity	NPD3664	Approved
0.6327	Remote Similarity	NPD3663	Approved
0.6327	Remote Similarity	NPD3662	Phase 3
0.6324	Remote Similarity	NPD4254	Approved
0.6324	Remote Similarity	NPD4253	Approved
0.6322	Remote Similarity	NPD8407	Phase 2
0.6319	Remote Similarity	NPD6624	Discontinued
0.6316	Remote Similarity	NPD5190	Phase 2
0.6316	Remote Similarity	NPD1040	Phase 2
0.6312	Remote Similarity	NPD1759	Phase 1
0.6312	Remote Similarity	NPD7741	Discontinued
0.6309	Remote Similarity	NPD8011	Discontinued
0.6306	Remote Similarity	NPD7236	Approved
0.6304	Remote Similarity	NPD2652	Approved
0.6304	Remote Similarity	NPD2650	Approved
0.6299	Remote Similarity	NPD3719	Approved
0.6299	Remote Similarity	NPD3718	Approved
0.6294	Remote Similarity	NPD4136	Approved
0.6294	Remote Similarity	NPD4135	Approved
0.6294	Remote Similarity	NPD4106	Approved
0.6291	Remote Similarity	NPD4684	Phase 3
0.6291	Remote Similarity	NPD8643	Discontinued
0.6291	Remote Similarity	NPD4685	Phase 3
0.6291	Remote Similarity	NPD4686	Approved
0.6288	Remote Similarity	NPD5765	Approved
0.6288	Remote Similarity	NPD1542	Approved
0.6288	Remote Similarity	NPD4229	Approved
0.6288	Remote Similarity	NPD4231	Approved
0.6288	Remote Similarity	NPD4656	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