NPASS Compound

Structure

NPC52951 OpenBabel07101719252D 38 42 0 0 1 0 0 0 0 0999 V2000 11.7949 1.2525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1550 2.9467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8604 1.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4179 1.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9696 2.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1665 3.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1720 3.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5077 2.4114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2206 3.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4859 2.2035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5514 2.8272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1987 3.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5733 3.0352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0981 2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3660 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8301 2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9641 2.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2321 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8678 4.1056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 4 26 1 0 0 0 0 6 7 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 27 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 28 1 0 0 0 0 18 37 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 21 32 2 0 0 0 0 22 26 1 6 0 0 0 23 27 1 1 0 0 0 23 30 1 0 0 0 0 24 28 1 6 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 25 33 2 0 0 0 0 26 27 1 6 0 0 0 27 5 1 1 0 0 0 28 17 1 6 0 0 0 29 30 1 1 0 0 0 30 13 1 1 0 0 0 34 38 1 0 0 0 0 35 38 2 0 0 0 0 36 38 2 0 0 0 0 37 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.31
Volume:	559.421
LogP:	2.873
LogD:	3.175
LogS:	-2.969
# Rotatable Bonds:	9
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	5.894
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.313
MDCK Permeability:	8.478722520521842e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.654
Plasma Protein Binding (PPB):	90.95691680908203%
Volume Distribution (VD):	0.86
Pgp-substrate:	1.9532674551010132%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.362
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	5.348
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.75
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.501
Skin Sensitization:	0.874
Carcinogencity:	0.79
Eye Corrosion:	0.021
Eye Irritation:	0.053
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC52951

Natural Product ID:	NPC52951
*Common Name:**	Capisterone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CCRYNKGKKAVQTA-JNRXYXSHSA-N
Standard InCHI:	InChI=1S/C30H48O7S/c1-19(2)14-21(32)15-20(3)22-8-10-27(5)23-6-7-24-28(17-31,18-37-38(34,35)36)25(33)9-11-29(24)16-30(23,29)13-12-26(22,27)4/h19-20,22-24,31H,6-18H2,1-5H3,(H,34,35,36)/t20-,22-,23+,24+,26-,27+,28+,29-,30+/m1/s1
SMILES:	CC(C)CC(=O)C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@](CO)(COS(=O)(=O)O)C(=O)CC[C@]54C[C@@]35CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162327
PubChem CID:	11620953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO7846	Penicillus capitatus	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643022]
NPO7846	Penicillus capitatus	Species	Udoteaceae	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	3
Others	3

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.33	n.a.	PMID[547808]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.15	n.a.	PMID[547808]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.5	n.a.	PMID[547808]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	7000.0	nM	PMID[547808]

☑ 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 NPC52951 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	334
0.1-0.2	3791
0.2-0.3	15629
0.3-0.4	9598
0.4-0.5	6379
0.5-0.6	5107
0.6-0.7	1498
0.7-0.8	320
0.8-0.85	33
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9041	High Similarity	NPC473267
0.875	High Similarity	NPC15821
0.8701	High Similarity	NPC264602
0.8553	High Similarity	NPC477930
0.8462	Intermediate Similarity	NPC477918
0.8442	Intermediate Similarity	NPC273366
0.84	Intermediate Similarity	NPC476731
0.8354	Intermediate Similarity	NPC329117
0.8354	Intermediate Similarity	NPC478128
0.8333	Intermediate Similarity	NPC477932
0.8333	Intermediate Similarity	NPC477933
0.8289	Intermediate Similarity	NPC126642
0.8289	Intermediate Similarity	NPC320549
0.8289	Intermediate Similarity	NPC156277
0.8289	Intermediate Similarity	NPC58057
0.8289	Intermediate Similarity	NPC151018
0.8228	Intermediate Similarity	NPC475031
0.8205	Intermediate Similarity	NPC477934
0.8193	Intermediate Similarity	NPC319909
0.8182	Intermediate Similarity	NPC310766
0.8182	Intermediate Similarity	NPC232112
0.8158	Intermediate Similarity	NPC477850
0.8133	Intermediate Similarity	NPC474954
0.8077	Intermediate Similarity	NPC254340
0.8077	Intermediate Similarity	NPC472854
0.8072	Intermediate Similarity	NPC472744
0.8049	Intermediate Similarity	NPC469745
0.8026	Intermediate Similarity	NPC324607
0.8026	Intermediate Similarity	NPC474962
0.8026	Intermediate Similarity	NPC131892
0.8026	Intermediate Similarity	NPC213178
0.8026	Intermediate Similarity	NPC252032
0.8026	Intermediate Similarity	NPC321732
0.8026	Intermediate Similarity	NPC319671
0.8026	Intermediate Similarity	NPC476734
0.8026	Intermediate Similarity	NPC327728
0.8026	Intermediate Similarity	NPC469941
0.8026	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC302111
0.7976	Intermediate Similarity	NPC50438
0.7975	Intermediate Similarity	NPC472311
0.7975	Intermediate Similarity	NPC174964
0.7975	Intermediate Similarity	NPC97534
0.7975	Intermediate Similarity	NPC125767
0.7975	Intermediate Similarity	NPC21220
0.7975	Intermediate Similarity	NPC195155
0.7952	Intermediate Similarity	NPC477935
0.7922	Intermediate Similarity	NPC477929
0.7901	Intermediate Similarity	NPC185465
0.7895	Intermediate Similarity	NPC473225
0.7875	Intermediate Similarity	NPC5767
0.7875	Intermediate Similarity	NPC472487
0.7875	Intermediate Similarity	NPC4209
0.7875	Intermediate Similarity	NPC475742
0.7875	Intermediate Similarity	NPC472486
0.7857	Intermediate Similarity	NPC268578
0.7857	Intermediate Similarity	NPC217559
0.7857	Intermediate Similarity	NPC292458
0.7848	Intermediate Similarity	NPC478130
0.7848	Intermediate Similarity	NPC167702
0.7848	Intermediate Similarity	NPC280026
0.7838	Intermediate Similarity	NPC128608
0.7831	Intermediate Similarity	NPC12933
0.7821	Intermediate Similarity	NPC469940
0.7821	Intermediate Similarity	NPC89310
0.7805	Intermediate Similarity	NPC320144
0.7791	Intermediate Similarity	NPC472745
0.7791	Intermediate Similarity	NPC474448
0.7778	Intermediate Similarity	NPC23884
0.7778	Intermediate Similarity	NPC477919
0.7778	Intermediate Similarity	NPC317913
0.7778	Intermediate Similarity	NPC221420
0.7778	Intermediate Similarity	NPC180199
0.7778	Intermediate Similarity	NPC207010
0.7765	Intermediate Similarity	NPC473336
0.7765	Intermediate Similarity	NPC471044
0.7763	Intermediate Similarity	NPC478180
0.7763	Intermediate Similarity	NPC130459
0.7763	Intermediate Similarity	NPC474221
0.775	Intermediate Similarity	NPC179858
0.775	Intermediate Similarity	NPC212733
0.775	Intermediate Similarity	NPC27349
0.775	Intermediate Similarity	NPC24014
0.7738	Intermediate Similarity	NPC317066
0.7738	Intermediate Similarity	NPC477936
0.7738	Intermediate Similarity	NPC477858
0.7738	Intermediate Similarity	NPC328007
0.7727	Intermediate Similarity	NPC56962
0.7727	Intermediate Similarity	NPC24705
0.7722	Intermediate Similarity	NPC474123
0.7711	Intermediate Similarity	NPC470609
0.7701	Intermediate Similarity	NPC263802
0.7701	Intermediate Similarity	NPC202937
0.7692	Intermediate Similarity	NPC108131
0.7683	Intermediate Similarity	NPC476732
0.7683	Intermediate Similarity	NPC34046
0.7683	Intermediate Similarity	NPC80089
0.7683	Intermediate Similarity	NPC171426
0.7683	Intermediate Similarity	NPC224802
0.7683	Intermediate Similarity	NPC199965
0.7683	Intermediate Similarity	NPC324700
0.7674	Intermediate Similarity	NPC201655
0.7662	Intermediate Similarity	NPC180777
0.7662	Intermediate Similarity	NPC260319
0.7662	Intermediate Similarity	NPC2568
0.7662	Intermediate Similarity	NPC103647
0.7647	Intermediate Similarity	NPC327451
0.7632	Intermediate Similarity	NPC477931
0.7632	Intermediate Similarity	NPC268736
0.7632	Intermediate Similarity	NPC42060
0.7625	Intermediate Similarity	NPC133922
0.7619	Intermediate Similarity	NPC77311
0.7614	Intermediate Similarity	NPC146937
0.759	Intermediate Similarity	NPC80891
0.759	Intermediate Similarity	NPC201459
0.759	Intermediate Similarity	NPC201276
0.7586	Intermediate Similarity	NPC70661
0.7564	Intermediate Similarity	NPC64466
0.7561	Intermediate Similarity	NPC298168
0.7561	Intermediate Similarity	NPC143133
0.7558	Intermediate Similarity	NPC474996
0.7532	Intermediate Similarity	NPC473230
0.7532	Intermediate Similarity	NPC475884
0.7531	Intermediate Similarity	NPC159789
0.7529	Intermediate Similarity	NPC61107
0.7529	Intermediate Similarity	NPC30583
0.7529	Intermediate Similarity	NPC289486
0.7528	Intermediate Similarity	NPC61688
0.75	Intermediate Similarity	NPC477851
0.75	Intermediate Similarity	NPC134197
0.75	Intermediate Similarity	NPC252714
0.75	Intermediate Similarity	NPC266431
0.75	Intermediate Similarity	NPC472853
0.7471	Intermediate Similarity	NPC76518
0.7444	Intermediate Similarity	NPC476296
0.7442	Intermediate Similarity	NPC259173
0.7416	Intermediate Similarity	NPC226491
0.7416	Intermediate Similarity	NPC183374
0.7416	Intermediate Similarity	NPC211162
0.7416	Intermediate Similarity	NPC477614
0.7412	Intermediate Similarity	NPC474484
0.7412	Intermediate Similarity	NPC103754
0.7397	Intermediate Similarity	NPC476735
0.7386	Intermediate Similarity	NPC92139
0.7381	Intermediate Similarity	NPC245029
0.7381	Intermediate Similarity	NPC472310
0.7381	Intermediate Similarity	NPC31302
0.7375	Intermediate Similarity	NPC290058
0.7375	Intermediate Similarity	NPC472309
0.7375	Intermediate Similarity	NPC478103
0.7368	Intermediate Similarity	NPC69149
0.7356	Intermediate Similarity	NPC25037
0.7356	Intermediate Similarity	NPC34984
0.7349	Intermediate Similarity	NPC106078
0.7349	Intermediate Similarity	NPC471151
0.7349	Intermediate Similarity	NPC474404
0.7342	Intermediate Similarity	NPC196197
0.734	Intermediate Similarity	NPC156546
0.7333	Intermediate Similarity	NPC213832
0.7333	Intermediate Similarity	NPC271974
0.7333	Intermediate Similarity	NPC247312
0.7333	Intermediate Similarity	NPC57954
0.7326	Intermediate Similarity	NPC121121
0.7326	Intermediate Similarity	NPC145143
0.7326	Intermediate Similarity	NPC46881
0.7326	Intermediate Similarity	NPC110780
0.7326	Intermediate Similarity	NPC268040
0.7317	Intermediate Similarity	NPC132064
0.7312	Intermediate Similarity	NPC263135
0.7312	Intermediate Similarity	NPC288906
0.7303	Intermediate Similarity	NPC57469
0.7303	Intermediate Similarity	NPC96496
0.7294	Intermediate Similarity	NPC261616
0.7284	Intermediate Similarity	NPC68426
0.7284	Intermediate Similarity	NPC477229
0.7284	Intermediate Similarity	NPC282905
0.7284	Intermediate Similarity	NPC81759
0.7283	Intermediate Similarity	NPC476189
0.7273	Intermediate Similarity	NPC473276
0.7273	Intermediate Similarity	NPC474380
0.7273	Intermediate Similarity	NPC41577
0.7253	Intermediate Similarity	NPC475056
0.7241	Intermediate Similarity	NPC475726
0.7241	Intermediate Similarity	NPC471036
0.7241	Intermediate Similarity	NPC163616
0.7241	Intermediate Similarity	NPC472743
0.7241	Intermediate Similarity	NPC175410
0.7241	Intermediate Similarity	NPC291320
0.7241	Intermediate Similarity	NPC86370
0.7237	Intermediate Similarity	NPC114891
0.7234	Intermediate Similarity	NPC234564
0.7234	Intermediate Similarity	NPC29152
0.7229	Intermediate Similarity	NPC108840
0.7222	Intermediate Similarity	NPC471900
0.7209	Intermediate Similarity	NPC58631
0.7209	Intermediate Similarity	NPC50658
0.7204	Intermediate Similarity	NPC206878
0.7195	Intermediate Similarity	NPC130011
0.7195	Intermediate Similarity	NPC159325
0.7195	Intermediate Similarity	NPC168511

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 NPC52951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	3757
0.2-0.3	3624
0.3-0.4	832
0.4-0.5	265
0.5-0.6	238
0.6-0.7	59
0.7-0.8	20
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD4789	Approved
0.8289	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4245	Approved
0.8158	Intermediate Similarity	NPD4244	Approved
0.8026	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3698	Phase 2
0.7901	Intermediate Similarity	NPD5364	Discontinued
0.7895	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5360	Phase 3
0.7875	Intermediate Similarity	NPD6117	Approved
0.7848	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6081	Approved
0.7778	Intermediate Similarity	NPD6116	Phase 1
0.7683	Intermediate Similarity	NPD6118	Approved
0.7683	Intermediate Similarity	NPD6697	Approved
0.7683	Intermediate Similarity	NPD6114	Approved
0.7683	Intermediate Similarity	NPD6115	Approved
0.7632	Intermediate Similarity	NPD4224	Phase 2
0.7531	Intermediate Similarity	NPD3703	Phase 2
0.7375	Intermediate Similarity	NPD4758	Discontinued
0.7262	Intermediate Similarity	NPD3671	Phase 1
0.7241	Intermediate Similarity	NPD4788	Approved
0.716	Intermediate Similarity	NPD5777	Approved
0.7125	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3702	Approved
0.6966	Remote Similarity	NPD3668	Phase 3
0.6966	Remote Similarity	NPD4786	Approved
0.6889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4753	Phase 2
0.6742	Remote Similarity	NPD3667	Approved
0.6627	Remote Similarity	NPD4787	Phase 1
0.6596	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD3133	Approved
0.6593	Remote Similarity	NPD3665	Phase 1
0.6477	Remote Similarity	NPD3617	Approved
0.6465	Remote Similarity	NPD6083	Phase 2
0.6465	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD8035	Phase 2
0.6458	Remote Similarity	NPD8034	Phase 2
0.6458	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4629	Approved
0.6392	Remote Similarity	NPD6399	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6344	Remote Similarity	NPD5329	Approved
0.63	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD5279	Phase 3
0.6264	Remote Similarity	NPD4692	Approved
0.6264	Remote Similarity	NPD4139	Approved
0.625	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4197	Approved
0.6224	Remote Similarity	NPD4202	Approved
0.6203	Remote Similarity	NPD3198	Approved
0.62	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5222	Approved
0.62	Remote Similarity	NPD5221	Approved
0.62	Remote Similarity	NPD4697	Phase 3
0.619	Remote Similarity	NPD6705	Phase 1
0.6186	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6700	Approved
0.6176	Remote Similarity	NPD5285	Approved
0.6176	Remote Similarity	NPD5286	Approved
0.6176	Remote Similarity	NPD8418	Phase 2
0.6176	Remote Similarity	NPD4700	Approved
0.6176	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD7525	Registered
0.6146	Remote Similarity	NPD6672	Approved
0.6146	Remote Similarity	NPD5737	Approved
0.6139	Remote Similarity	NPD5173	Approved
0.6122	Remote Similarity	NPD6702	Approved
0.6122	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD6703	Approved
0.6105	Remote Similarity	NPD5205	Approved
0.6105	Remote Similarity	NPD4690	Approved
0.6105	Remote Similarity	NPD4689	Approved
0.6105	Remote Similarity	NPD4688	Approved
0.6105	Remote Similarity	NPD4138	Approved
0.6105	Remote Similarity	NPD4693	Phase 3
0.61	Remote Similarity	NPD5695	Phase 3
0.6078	Remote Similarity	NPD5696	Approved
0.6058	Remote Similarity	NPD4633	Approved
0.6058	Remote Similarity	NPD5211	Phase 2
0.6058	Remote Similarity	NPD5225	Approved
0.6058	Remote Similarity	NPD5226	Approved
0.6058	Remote Similarity	NPD5224	Approved
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD6920	Discontinued
0.6038	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.5979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6928	Phase 2
0.5974	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4634	Approved
0.5962	Remote Similarity	NPD5223	Approved
0.5955	Remote Similarity	NPD7339	Approved
0.5955	Remote Similarity	NPD6942	Approved
0.5943	Remote Similarity	NPD5141	Approved
0.5941	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5280	Approved
0.5938	Remote Similarity	NPD7146	Approved
0.5938	Remote Similarity	NPD7521	Approved
0.5938	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD6684	Approved
0.5938	Remote Similarity	NPD4694	Approved
0.5938	Remote Similarity	NPD5690	Phase 2
0.5938	Remote Similarity	NPD5330	Approved
0.5938	Remote Similarity	NPD7334	Approved
0.5934	Remote Similarity	NPD4802	Phase 2
0.5934	Remote Similarity	NPD4238	Approved
0.5929	Remote Similarity	NPD7115	Discovery
0.5926	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5926	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD5133	Approved
0.5888	Remote Similarity	NPD4768	Approved
0.5888	Remote Similarity	NPD4767	Approved
0.5872	Remote Similarity	NPD6372	Approved
0.5872	Remote Similarity	NPD6373	Approved
0.5842	Remote Similarity	NPD7748	Approved
0.5833	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD6412	Phase 2
0.5825	Remote Similarity	NPD7920	Phase 3
0.5825	Remote Similarity	NPD7919	Phase 3
0.5818	Remote Similarity	NPD7102	Approved
0.5818	Remote Similarity	NPD7290	Approved
0.5818	Remote Similarity	NPD6883	Approved
0.5816	Remote Similarity	NPD6903	Approved
0.5806	Remote Similarity	NPD4695	Discontinued
0.58	Remote Similarity	NPD5281	Approved
0.58	Remote Similarity	NPD5284	Approved
0.578	Remote Similarity	NPD4729	Approved
0.578	Remote Similarity	NPD6415	Discontinued
0.578	Remote Similarity	NPD5128	Approved
0.578	Remote Similarity	NPD4730	Approved
0.5773	Remote Similarity	NPD6098	Approved
0.5769	Remote Similarity	NPD8088	Phase 1
0.5769	Remote Similarity	NPD7638	Approved
0.5769	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6869	Approved
0.5766	Remote Similarity	NPD6847	Approved
0.5766	Remote Similarity	NPD6617	Approved
0.5766	Remote Similarity	NPD6650	Approved
0.5766	Remote Similarity	NPD6649	Approved
0.5766	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8130	Phase 1
0.5761	Remote Similarity	NPD4777	Suspended
0.5761	Remote Similarity	NPD4776	Phase 2
0.5761	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6904	Approved
0.5758	Remote Similarity	NPD6080	Approved
0.5758	Remote Similarity	NPD6673	Approved
0.5758	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD6013	Approved
0.5727	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5699	Remote Similarity	NPD4195	Approved
0.5682	Remote Similarity	NPD4747	Approved
0.5676	Remote Similarity	NPD5251	Approved
0.5676	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5249	Phase 3
0.5676	Remote Similarity	NPD5248	Approved
0.5676	Remote Similarity	NPD5247	Approved
0.5676	Remote Similarity	NPD5135	Approved
0.5676	Remote Similarity	NPD5250	Approved
0.5673	Remote Similarity	NPD7902	Approved
0.5667	Remote Similarity	NPD6924	Approved
0.5667	Remote Similarity	NPD6926	Approved
0.566	Remote Similarity	NPD1700	Approved
0.5644	Remote Similarity	NPD7637	Suspended
0.5644	Remote Similarity	NPD6411	Approved
0.5641	Remote Similarity	NPD6054	Approved
0.5641	Remote Similarity	NPD6059	Approved
0.5636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6011	Approved
0.5636	Remote Similarity	NPD5168	Approved
0.5625	Remote Similarity	NPD5217	Approved
0.5625	Remote Similarity	NPD5216	Approved
0.5625	Remote Similarity	NPD5215	Approved
0.5618	Remote Similarity	NPD4243	Approved
0.5612	Remote Similarity	NPD4623	Approved
0.5612	Remote Similarity	NPD4519	Discontinued
0.5607	Remote Similarity	NPD7632	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