NPASS Compound

Structure

NPC474004 OpenBabel07101719132D 32 35 0 0 1 0 0 0 0 0999 V2000 2.2321 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -7.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -6.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 31 1 0 0 0 0 11 14 1 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 32 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 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 2 0 0 0 0 21 28 1 0 0 0 0 22 29 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.15
Volume:	453.591
LogP:	4.963
LogD:	3.09
LogS:	-3.891
# Rotatable Bonds:	4
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	4.437
Fsp3:	0.4
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:	-4.804
MDCK Permeability:	1.2246466212673113e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.156
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	91.65230560302734%
Volume Distribution (VD):	0.841
Pgp-substrate:	6.3797807693481445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.52
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.279
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	1.632
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.523
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.569
Rat Oral Acute Toxicity:	0.547
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.377
Carcinogencity:	0.863
Eye Corrosion:	0.003
Eye Irritation:	0.122
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC474004

Natural Product ID:	NPC474004
*Common Name:**	15-Chlorotajixanthone Hydrate
IUPAC Name:	(1R,2S)-8-[(2S)-2-chloro-3-hydroxy-3-methylbutyl]-1,11-dihydroxy-5-methyl-2-prop-1-en-2-yl-2,3-dihydro-1H-pyrano[3,2-a]xanthen-12-one;hydrate
Synonyms:	15-Chlorotajixanthone Hydrate
Standard InCHIKey:	FTKJGBFCWTZCCQ-OKLLSCIYSA-N
Standard InCHI:	InChI=1S/C25H27ClO6.H2O/c1-11(2)14-10-31-23-12(3)8-16-19(20(23)21(14)28)22(29)18-15(27)7-6-13(24(18)32-16)9-17(26)25(4,5)30;/h6-8,14,17,21,27-28,30H,1,9-10H2,2-5H3;1H2/t14-,17+,21-;/m1./s1
SMILES:	CC(=C)[C@H]1COc2c([C@@H]1O)c1c(cc2C)oc2c(c1=O)c(O)ccc2C[C@@H](C(O)(C)C)Cl.O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458017
PubChem CID:	44581697
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17323993]
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013822]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1621	Individual Protein	Calmodulin	Homo sapiens	IC50	=	9590.0	nM	PMID[482665]

☑ 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 NPC474004 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	457
0.1-0.2	1799
0.2-0.3	4026
0.3-0.4	10330
0.4-0.5	8515
0.5-0.6	4227
0.6-0.7	5669
0.7-0.8	5464
0.8-0.85	1981
0.85-0.9	218
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC186113
0.9379	High Similarity	NPC473961
0.9182	High Similarity	NPC135522
0.9152	High Similarity	NPC225419
0.9042	High Similarity	NPC241874
0.8916	High Similarity	NPC477834
0.8896	High Similarity	NPC44199
0.8882	High Similarity	NPC474843
0.8862	High Similarity	NPC178173
0.8827	High Similarity	NPC178964
0.8827	High Similarity	NPC280530
0.8827	High Similarity	NPC95842
0.8805	High Similarity	NPC71055
0.8788	High Similarity	NPC471976
0.8765	High Similarity	NPC87708
0.8758	High Similarity	NPC227122
0.8758	High Similarity	NPC202595
0.8735	High Similarity	NPC3629
0.8704	High Similarity	NPC232645
0.8704	High Similarity	NPC72958
0.8698	High Similarity	NPC6588
0.8698	High Similarity	NPC477154
0.8698	High Similarity	NPC117854
0.8696	High Similarity	NPC473016
0.869	High Similarity	NPC25361
0.8683	High Similarity	NPC472402
0.8667	High Similarity	NPC281137
0.8667	High Similarity	NPC282390
0.8659	High Similarity	NPC55662
0.8659	High Similarity	NPC166054
0.865	High Similarity	NPC281272
0.8642	High Similarity	NPC37348
0.8642	High Similarity	NPC471115
0.8642	High Similarity	NPC472633
0.8642	High Similarity	NPC29777
0.8639	High Similarity	NPC120593
0.8634	High Similarity	NPC5537
0.8631	High Similarity	NPC207690
0.8631	High Similarity	NPC197168
0.8625	High Similarity	NPC469758
0.8623	High Similarity	NPC18380
0.8623	High Similarity	NPC137232
0.8613	High Similarity	NPC324220
0.8613	High Similarity	NPC312630
0.8606	High Similarity	NPC164427
0.8605	High Similarity	NPC154986
0.8598	High Similarity	NPC169990
0.8598	High Similarity	NPC329844
0.8598	High Similarity	NPC210942
0.8589	High Similarity	NPC473131
0.8589	High Similarity	NPC478148
0.8589	High Similarity	NPC470675
0.8589	High Similarity	NPC207346
0.8589	High Similarity	NPC149526
0.8589	High Similarity	NPC474417
0.8589	High Similarity	NPC46564
0.8588	High Similarity	NPC474024
0.858	High Similarity	NPC266499
0.8571	High Similarity	NPC229632
0.8571	High Similarity	NPC15374
0.8571	High Similarity	NPC308200
0.8563	High Similarity	NPC292863
0.8563	High Similarity	NPC470810
0.8563	High Similarity	NPC184326
0.8563	High Similarity	NPC472618
0.8562	High Similarity	NPC469764
0.8554	High Similarity	NPC196448
0.8554	High Similarity	NPC272196
0.8545	High Similarity	NPC175192
0.8537	High Similarity	NPC475790
0.8537	High Similarity	NPC40356
0.8537	High Similarity	NPC154683
0.8529	High Similarity	NPC128293
0.8529	High Similarity	NPC37870
0.8529	High Similarity	NPC43319
0.8529	High Similarity	NPC272502
0.8528	High Similarity	NPC120105
0.8528	High Similarity	NPC101957
0.8521	High Similarity	NPC273959
0.8521	High Similarity	NPC290160
0.8521	High Similarity	NPC236521
0.8521	High Similarity	NPC152659
0.8521	High Similarity	NPC248638
0.8519	High Similarity	NPC37135
0.8519	High Similarity	NPC39195
0.8519	High Similarity	NPC145467
0.8519	High Similarity	NPC186397
0.8512	High Similarity	NPC474187
0.8512	High Similarity	NPC474186
0.8509	High Similarity	NPC24136
0.8509	High Similarity	NPC473132
0.8509	High Similarity	NPC290133
0.8509	High Similarity	NPC472629
0.8509	High Similarity	NPC473135
0.8509	High Similarity	NPC470676
0.8509	High Similarity	NPC187282
0.8503	High Similarity	NPC329091
0.8503	High Similarity	NPC472617
0.8503	High Similarity	NPC195167
0.8503	High Similarity	NPC85121
0.8503	High Similarity	NPC226287
0.8488	Intermediate Similarity	NPC103307
0.8488	Intermediate Similarity	NPC241387
0.8488	Intermediate Similarity	NPC251144
0.8485	Intermediate Similarity	NPC477691
0.8485	Intermediate Similarity	NPC193200
0.848	Intermediate Similarity	NPC218226
0.8476	Intermediate Similarity	NPC470569
0.8476	Intermediate Similarity	NPC474023
0.8476	Intermediate Similarity	NPC474021
0.8476	Intermediate Similarity	NPC39819
0.8471	Intermediate Similarity	NPC239752
0.8471	Intermediate Similarity	NPC293319
0.8471	Intermediate Similarity	NPC472450
0.8471	Intermediate Similarity	NPC275780
0.8466	Intermediate Similarity	NPC158338
0.8466	Intermediate Similarity	NPC10027
0.8466	Intermediate Similarity	NPC97028
0.8466	Intermediate Similarity	NPC288036
0.8466	Intermediate Similarity	NPC329933
0.8466	Intermediate Similarity	NPC65775
0.8466	Intermediate Similarity	NPC100985
0.8466	Intermediate Similarity	NPC65589
0.8466	Intermediate Similarity	NPC97029
0.8466	Intermediate Similarity	NPC471114
0.8466	Intermediate Similarity	NPC5173
0.8466	Intermediate Similarity	NPC223988
0.8462	Intermediate Similarity	NPC329760
0.8462	Intermediate Similarity	NPC52204
0.8462	Intermediate Similarity	NPC25152
0.8462	Intermediate Similarity	NPC473022
0.8457	Intermediate Similarity	NPC477683
0.8457	Intermediate Similarity	NPC473077
0.8457	Intermediate Similarity	NPC477682
0.8457	Intermediate Similarity	NPC296998
0.8452	Intermediate Similarity	NPC475886
0.8452	Intermediate Similarity	NPC321399
0.8452	Intermediate Similarity	NPC474287
0.8452	Intermediate Similarity	NPC284495
0.8452	Intermediate Similarity	NPC119224
0.8447	Intermediate Similarity	NPC470890
0.8447	Intermediate Similarity	NPC271288
0.8447	Intermediate Similarity	NPC124780
0.8447	Intermediate Similarity	NPC311144
0.8447	Intermediate Similarity	NPC131568
0.8447	Intermediate Similarity	NPC87486
0.8447	Intermediate Similarity	NPC131579
0.8443	Intermediate Similarity	NPC217677
0.8443	Intermediate Similarity	NPC475184
0.8443	Intermediate Similarity	NPC165977
0.8443	Intermediate Similarity	NPC471209
0.8439	Intermediate Similarity	NPC472620
0.8434	Intermediate Similarity	NPC477958
0.8434	Intermediate Similarity	NPC68727
0.8434	Intermediate Similarity	NPC275575
0.843	Intermediate Similarity	NPC297195
0.843	Intermediate Similarity	NPC207574
0.843	Intermediate Similarity	NPC291795
0.8424	Intermediate Similarity	NPC477690
0.8424	Intermediate Similarity	NPC51824
0.8424	Intermediate Similarity	NPC217447
0.8424	Intermediate Similarity	NPC470340
0.8424	Intermediate Similarity	NPC253904
0.8424	Intermediate Similarity	NPC273483
0.8424	Intermediate Similarity	NPC268992
0.8424	Intermediate Similarity	NPC321363
0.8424	Intermediate Similarity	NPC113608
0.8424	Intermediate Similarity	NPC470338
0.8424	Intermediate Similarity	NPC142527
0.8424	Intermediate Similarity	NPC470337
0.8421	Intermediate Similarity	NPC170245
0.8421	Intermediate Similarity	NPC39091
0.8421	Intermediate Similarity	NPC173292
0.8421	Intermediate Similarity	NPC251336
0.8421	Intermediate Similarity	NPC472449
0.8415	Intermediate Similarity	NPC255641
0.8415	Intermediate Similarity	NPC294646
0.8415	Intermediate Similarity	NPC470568
0.8415	Intermediate Similarity	NPC290954
0.8415	Intermediate Similarity	NPC147735
0.8412	Intermediate Similarity	NPC7483
0.8412	Intermediate Similarity	NPC236132
0.8412	Intermediate Similarity	NPC189473
0.8412	Intermediate Similarity	NPC23298
0.8412	Intermediate Similarity	NPC100849
0.8412	Intermediate Similarity	NPC186686
0.8405	Intermediate Similarity	NPC256672
0.8405	Intermediate Similarity	NPC106328
0.8405	Intermediate Similarity	NPC191634
0.8405	Intermediate Similarity	NPC27221
0.8405	Intermediate Similarity	NPC7025
0.8405	Intermediate Similarity	NPC35150
0.8402	Intermediate Similarity	NPC475883
0.8402	Intermediate Similarity	NPC66288
0.8402	Intermediate Similarity	NPC472632
0.8402	Intermediate Similarity	NPC32694
0.8402	Intermediate Similarity	NPC474351
0.8402	Intermediate Similarity	NPC61010
0.84	Intermediate Similarity	NPC475246
0.8395	Intermediate Similarity	NPC54577

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 NPC474004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	1019
0.2-0.3	1672
0.3-0.4	2714
0.4-0.5	1980
0.5-0.6	900
0.6-0.7	317
0.7-0.8	143
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD6959	Discontinued
0.8263	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5494	Approved
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1934	Approved
0.7963	Intermediate Similarity	NPD1549	Phase 2
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD2801	Approved
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7892	Intermediate Similarity	NPD2534	Approved
0.7892	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2532	Approved
0.7892	Intermediate Similarity	NPD2533	Approved
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD6232	Discontinued
0.7824	Intermediate Similarity	NPD7411	Suspended
0.7809	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7075	Discontinued
0.7796	Intermediate Similarity	NPD4363	Phase 3
0.7796	Intermediate Similarity	NPD4360	Phase 2
0.7791	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD2346	Discontinued
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7758	Intermediate Similarity	NPD3750	Approved
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.7733	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2796	Approved
0.773	Intermediate Similarity	NPD2935	Discontinued
0.7709	Intermediate Similarity	NPD7054	Approved
0.7706	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD3749	Approved
0.7669	Intermediate Similarity	NPD1510	Phase 2
0.7667	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6797	Phase 2
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD1511	Approved
0.7582	Intermediate Similarity	NPD7251	Discontinued
0.7572	Intermediate Similarity	NPD6801	Discontinued
0.7562	Intermediate Similarity	NPD4625	Phase 3
0.7561	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3818	Discontinued
0.7545	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3882	Suspended
0.7541	Intermediate Similarity	NPD7808	Phase 3
0.7531	Intermediate Similarity	NPD1240	Approved
0.7529	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.7485	Intermediate Similarity	NPD2800	Approved
0.7474	Intermediate Similarity	NPD7698	Approved
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7474	Intermediate Similarity	NPD7697	Approved
0.7457	Intermediate Similarity	NPD6599	Discontinued
0.7455	Intermediate Similarity	NPD3748	Approved
0.7455	Intermediate Similarity	NPD2799	Discontinued
0.743	Intermediate Similarity	NPD5710	Approved
0.743	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4908	Phase 1
0.7387	Intermediate Similarity	NPD7783	Phase 2
0.7387	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3817	Phase 2
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.7384	Intermediate Similarity	NPD5403	Approved
0.7382	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD4361	Phase 2
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.733	Intermediate Similarity	NPD1465	Phase 2
0.7323	Intermediate Similarity	NPD7701	Phase 2
0.731	Intermediate Similarity	NPD6799	Approved
0.7301	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD5401	Approved
0.7247	Intermediate Similarity	NPD4967	Phase 2
0.7247	Intermediate Similarity	NPD4966	Approved
0.7247	Intermediate Similarity	NPD4965	Approved
0.724	Intermediate Similarity	NPD6535	Approved
0.724	Intermediate Similarity	NPD6534	Approved
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7216	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7214	Intermediate Similarity	NPD7801	Approved
0.7202	Intermediate Similarity	NPD5406	Approved
0.7202	Intermediate Similarity	NPD5408	Approved
0.7202	Intermediate Similarity	NPD5405	Approved
0.7202	Intermediate Similarity	NPD5404	Approved
0.72	Intermediate Similarity	NPD8151	Discontinued
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD4749	Approved
0.7184	Intermediate Similarity	NPD920	Approved
0.7182	Intermediate Similarity	NPD1247	Approved
0.7176	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1610	Phase 2
0.7168	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6234	Discontinued
0.7164	Intermediate Similarity	NPD7874	Approved
0.7164	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2403	Approved
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7003	Approved
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD6651	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1613	Approved
0.7105	Intermediate Similarity	NPD8434	Phase 2
0.7099	Intermediate Similarity	NPD1470	Approved
0.7091	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD2344	Approved
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5761	Phase 2
0.7039	Intermediate Similarity	NPD5760	Phase 2
0.7	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD8319	Approved
0.6977	Remote Similarity	NPD1243	Approved
0.6954	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2798	Approved
0.6944	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD4308	Phase 3
0.6941	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD1283	Approved
0.6931	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD6213	Phase 3
0.6923	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6212	Phase 3
0.6919	Remote Similarity	NPD2424	Discontinued
0.6919	Remote Similarity	NPD3926	Phase 2
0.6914	Remote Similarity	NPD7041	Phase 2
0.6914	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7458	Discontinued
0.6906	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD943	Approved
0.6905	Remote Similarity	NPD4060	Phase 1
0.6905	Remote Similarity	NPD2979	Phase 3
0.6902	Remote Similarity	NPD7199	Phase 2
0.6898	Remote Similarity	NPD7177	Discontinued
0.6897	Remote Similarity	NPD2309	Approved
0.689	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD1203	Approved
0.6886	Remote Similarity	NPD3764	Approved
0.6886	Remote Similarity	NPD3268	Approved
0.6885	Remote Similarity	NPD919	Approved
0.6882	Remote Similarity	NPD4536	Approved
0.6882	Remote Similarity	NPD4538	Approved
0.6882	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD6785	Approved
0.6867	Remote Similarity	NPD6832	Phase 2
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)

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