NPASS Compound

Structure

CID48671 OpenBabel06191715382D 33 37 0 0 1 0 0 0 0 0999 V2000 -5.0372 4.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4062 3.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 32 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 18 23 1 0 0 0 0 18 29 1 6 0 0 0 19 33 1 0 0 0 0 20 26 1 6 0 0 0 20 28 1 0 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 28 1 6 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 27 33 1 0 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.29
Volume:	483.467
LogP:	5.187
LogD:	4.14
LogS:	-4.811
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.624
Fsp3:	0.75
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:	-4.798
MDCK Permeability:	1.8994416677742265e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.097

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	94.78461456298828%
Volume Distribution (VD):	1.625
Pgp-substrate:	7.0188703536987305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.3
CYP2C9-substrate:	0.443
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.496
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	10.087
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.752
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.159
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.748
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.666
Carcinogencity:	0.035
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC48671

Natural Product ID:	NPC48671
*Common Name:**	Tolypodiol
IUPAC Name:	n.a.
Synonyms:	Tolypodiol
Standard InCHIKey:	NQNQLGPYASRQND-KNFPFGBTSA-N
Standard InCHI:	InChI=1S/C28H40O5/c1-25(2)11-10-22(30)28(5)20-9-12-27(4)21(26(20,3)15-18(29)23(25)28)14-17-13-16(24(31)32-6)7-8-19(17)33-27/h7-8,13,18,20-23,29-30H,9-12,14-15H2,1-6H3/t18-,20+,21+,22-,23+,26-,27+,28+/m1/s1
SMILES:	COC(=O)c1ccc2c(c1)C[C@@H]1[C@](O2)(C)CC[C@H]2[C@@]1(C)C[C@@H](O)[C@@H]1[C@]2(C)[C@H](O)CCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466166
PubChem CID:	177341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO40827	Cyanobacterium HT-58-2	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32282204]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8792625]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748382]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	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
ED50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	30.0	ug	PMID[457227]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	30.0	ug	PMID[457228]

☑ 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 NPC48671 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	345
0.1-0.2	1366
0.2-0.3	2664
0.3-0.4	5462
0.4-0.5	9612
0.5-0.6	8372
0.6-0.7	7403
0.7-0.8	7013
0.8-0.85	403
0.85-0.9	54
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9262	High Similarity	NPC140133
0.9122	High Similarity	NPC286038
0.906	High Similarity	NPC66991
0.8808	High Similarity	NPC477483
0.8808	High Similarity	NPC325032
0.8784	High Similarity	NPC184053
0.875	High Similarity	NPC279442
0.8733	High Similarity	NPC169942
0.8726	High Similarity	NPC4950
0.8726	High Similarity	NPC472299
0.8726	High Similarity	NPC472617
0.8726	High Similarity	NPC239118
0.8718	High Similarity	NPC7059
0.8707	High Similarity	NPC265335
0.8693	High Similarity	NPC212257
0.8693	High Similarity	NPC474305
0.8679	High Similarity	NPC473022
0.8671	High Similarity	NPC79571
0.8671	High Similarity	NPC472618
0.8667	High Similarity	NPC474599
0.8662	High Similarity	NPC474611
0.8634	High Similarity	NPC125465
0.8634	High Similarity	NPC472621
0.8627	High Similarity	NPC475848
0.8627	High Similarity	NPC474306
0.8627	High Similarity	NPC146388
0.8608	High Similarity	NPC8389
0.8599	High Similarity	NPC194499
0.8591	High Similarity	NPC172311
0.859	High Similarity	NPC62051
0.8581	High Similarity	NPC121615
0.8581	High Similarity	NPC294511
0.858	High Similarity	NPC472622
0.8571	High Similarity	NPC327962
0.8571	High Similarity	NPC41689
0.8571	High Similarity	NPC146014
0.8545	High Similarity	NPC294149
0.8544	High Similarity	NPC158542
0.8544	High Similarity	NPC123153
0.8537	High Similarity	NPC472620
0.8535	High Similarity	NPC41880
0.8535	High Similarity	NPC472807
0.8528	High Similarity	NPC472619
0.8523	High Similarity	NPC79372
0.8519	High Similarity	NPC200726
0.8516	High Similarity	NPC119252
0.8509	High Similarity	NPC277618
0.8509	High Similarity	NPC469395
0.8506	High Similarity	NPC473719
0.8491	Intermediate Similarity	NPC218818
0.8487	Intermediate Similarity	NPC260152
0.8481	Intermediate Similarity	NPC195954
0.8481	Intermediate Similarity	NPC88007
0.8481	Intermediate Similarity	NPC304692
0.8481	Intermediate Similarity	NPC477674
0.8476	Intermediate Similarity	NPC313304
0.8476	Intermediate Similarity	NPC472803
0.8466	Intermediate Similarity	NPC177362
0.8462	Intermediate Similarity	NPC470675
0.8462	Intermediate Similarity	NPC473131
0.8462	Intermediate Similarity	NPC124842
0.8462	Intermediate Similarity	NPC305965
0.8452	Intermediate Similarity	NPC228842
0.8452	Intermediate Similarity	NPC247219
0.8435	Intermediate Similarity	NPC213122
0.8418	Intermediate Similarity	NPC104736
0.8415	Intermediate Similarity	NPC202428
0.8415	Intermediate Similarity	NPC266545
0.8414	Intermediate Similarity	NPC109778
0.8411	Intermediate Similarity	NPC263337
0.8411	Intermediate Similarity	NPC121158
0.8408	Intermediate Similarity	NPC44606
0.8405	Intermediate Similarity	NPC296558
0.8405	Intermediate Similarity	NPC291742
0.8405	Intermediate Similarity	NPC255787
0.8397	Intermediate Similarity	NPC475890
0.8397	Intermediate Similarity	NPC261659
0.8395	Intermediate Similarity	NPC308156
0.8385	Intermediate Similarity	NPC18380
0.8385	Intermediate Similarity	NPC137232
0.8385	Intermediate Similarity	NPC97812
0.8377	Intermediate Similarity	NPC71821
0.8375	Intermediate Similarity	NPC15815
0.8367	Intermediate Similarity	NPC48929
0.8364	Intermediate Similarity	NPC193698
0.8364	Intermediate Similarity	NPC52598
0.8354	Intermediate Similarity	NPC477669
0.8354	Intermediate Similarity	NPC472799
0.8344	Intermediate Similarity	NPC317715
0.8344	Intermediate Similarity	NPC155552
0.8344	Intermediate Similarity	NPC316960
0.8344	Intermediate Similarity	NPC148945
0.8344	Intermediate Similarity	NPC78835
0.8344	Intermediate Similarity	NPC309512
0.8344	Intermediate Similarity	NPC204561
0.8344	Intermediate Similarity	NPC138149
0.8333	Intermediate Similarity	NPC116292
0.8333	Intermediate Similarity	NPC267469
0.8333	Intermediate Similarity	NPC87630
0.8333	Intermediate Similarity	NPC179128
0.8333	Intermediate Similarity	NPC475106
0.8323	Intermediate Similarity	NPC68848
0.8323	Intermediate Similarity	NPC292863
0.8323	Intermediate Similarity	NPC195136
0.8323	Intermediate Similarity	NPC184326
0.8322	Intermediate Similarity	NPC249817
0.8313	Intermediate Similarity	NPC323627
0.8313	Intermediate Similarity	NPC324358
0.8313	Intermediate Similarity	NPC475184
0.8313	Intermediate Similarity	NPC322459
0.8313	Intermediate Similarity	NPC148185
0.8313	Intermediate Similarity	NPC257166
0.8313	Intermediate Similarity	NPC272196
0.8313	Intermediate Similarity	NPC318527
0.8312	Intermediate Similarity	NPC471608
0.8312	Intermediate Similarity	NPC75295
0.8303	Intermediate Similarity	NPC286074
0.8303	Intermediate Similarity	NPC54903
0.8303	Intermediate Similarity	NPC102810
0.8302	Intermediate Similarity	NPC477671
0.8302	Intermediate Similarity	NPC159692
0.8302	Intermediate Similarity	NPC477687
0.8293	Intermediate Similarity	NPC263212
0.8293	Intermediate Similarity	NPC251336
0.8289	Intermediate Similarity	NPC93640
0.8289	Intermediate Similarity	NPC20631
0.8288	Intermediate Similarity	NPC86774
0.8288	Intermediate Similarity	NPC327457
0.8282	Intermediate Similarity	NPC290160
0.8282	Intermediate Similarity	NPC100849
0.8282	Intermediate Similarity	NPC45943
0.8282	Intermediate Similarity	NPC473009
0.828	Intermediate Similarity	NPC37642
0.8278	Intermediate Similarity	NPC476191
0.8278	Intermediate Similarity	NPC473988
0.8278	Intermediate Similarity	NPC76312
0.8278	Intermediate Similarity	NPC67003
0.8272	Intermediate Similarity	NPC283209
0.8269	Intermediate Similarity	NPC17600
0.8267	Intermediate Similarity	NPC475482
0.8267	Intermediate Similarity	NPC198621
0.8267	Intermediate Similarity	NPC477592
0.8267	Intermediate Similarity	NPC22676
0.8267	Intermediate Similarity	NPC216940
0.8261	Intermediate Similarity	NPC287559
0.8261	Intermediate Similarity	NPC51247
0.8261	Intermediate Similarity	NPC474373
0.8261	Intermediate Similarity	NPC195167
0.8261	Intermediate Similarity	NPC105584
0.8258	Intermediate Similarity	NPC216755
0.8255	Intermediate Similarity	NPC173569
0.8255	Intermediate Similarity	NPC477874
0.8255	Intermediate Similarity	NPC279463
0.825	Intermediate Similarity	NPC4547
0.825	Intermediate Similarity	NPC469507
0.825	Intermediate Similarity	NPC192587
0.825	Intermediate Similarity	NPC477675
0.8243	Intermediate Similarity	NPC126516
0.8242	Intermediate Similarity	NPC472660
0.8239	Intermediate Similarity	NPC121568
0.8232	Intermediate Similarity	NPC473010
0.8232	Intermediate Similarity	NPC310572
0.8231	Intermediate Similarity	NPC18798
0.8228	Intermediate Similarity	NPC178484
0.8228	Intermediate Similarity	NPC209142
0.8228	Intermediate Similarity	NPC477672
0.8228	Intermediate Similarity	NPC477673
0.8228	Intermediate Similarity	NPC469503
0.8228	Intermediate Similarity	NPC11892
0.8228	Intermediate Similarity	NPC312549
0.8221	Intermediate Similarity	NPC473012
0.8217	Intermediate Similarity	NPC471114
0.8217	Intermediate Similarity	NPC35160
0.8217	Intermediate Similarity	NPC104236
0.8217	Intermediate Similarity	NPC473016
0.8217	Intermediate Similarity	NPC164205
0.8217	Intermediate Similarity	NPC52931
0.8217	Intermediate Similarity	NPC162569
0.8212	Intermediate Similarity	NPC307883
0.8212	Intermediate Similarity	NPC202260
0.821	Intermediate Similarity	NPC121647
0.821	Intermediate Similarity	NPC226462
0.821	Intermediate Similarity	NPC98023
0.821	Intermediate Similarity	NPC188649
0.821	Intermediate Similarity	NPC18986
0.8207	Intermediate Similarity	NPC37512
0.8207	Intermediate Similarity	NPC121104
0.8205	Intermediate Similarity	NPC300988
0.8205	Intermediate Similarity	NPC142863
0.8205	Intermediate Similarity	NPC478018
0.8205	Intermediate Similarity	NPC10990
0.8204	Intermediate Similarity	NPC118128
0.82	Intermediate Similarity	NPC474610
0.8199	Intermediate Similarity	NPC1796
0.8199	Intermediate Similarity	NPC140952
0.8199	Intermediate Similarity	NPC208258
0.8199	Intermediate Similarity	NPC281137
0.8199	Intermediate Similarity	NPC282390
0.8194	Intermediate Similarity	NPC208293
0.8194	Intermediate Similarity	NPC474044

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 NPC48671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	884
0.2-0.3	1485
0.3-0.4	2454
0.4-0.5	2097
0.5-0.6	1228
0.6-0.7	544
0.7-0.8	150
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8533	High Similarity	NPD4628	Phase 3
0.8497	Intermediate Similarity	NPD6273	Approved
0.8467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7458	Discontinued
0.8411	Intermediate Similarity	NPD7003	Approved
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8217	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD8127	Discontinued
0.8125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7411	Suspended
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8025	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8455	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7975	Intermediate Similarity	NPD7075	Discontinued
0.7974	Intermediate Similarity	NPD2346	Discontinued
0.7961	Intermediate Similarity	NPD2799	Discontinued
0.7953	Intermediate Similarity	NPD8312	Approved
0.7953	Intermediate Similarity	NPD8313	Approved
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7097	Phase 1
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6599	Discontinued
0.7826	Intermediate Similarity	NPD4380	Phase 2
0.7821	Intermediate Similarity	NPD3750	Approved
0.7811	Intermediate Similarity	NPD7177	Discontinued
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD5760	Phase 2
0.7791	Intermediate Similarity	NPD5761	Phase 2
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1608	Approved
0.7736	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6801	Discontinued
0.7727	Intermediate Similarity	NPD3748	Approved
0.7722	Intermediate Similarity	NPD7236	Approved
0.7714	Intermediate Similarity	NPD8434	Phase 2
0.7707	Intermediate Similarity	NPD8166	Discontinued
0.7697	Intermediate Similarity	NPD4140	Approved
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7677	Intermediate Similarity	NPD2796	Approved
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5494	Approved
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3749	Approved
0.7647	Intermediate Similarity	NPD5124	Phase 1
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.7647	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7473	Discontinued
0.7632	Intermediate Similarity	NPD8032	Phase 2
0.7628	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7613	Intermediate Similarity	NPD7033	Discontinued
0.7588	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7229	Phase 3
0.7574	Intermediate Similarity	NPD6232	Discontinued
0.7566	Intermediate Similarity	NPD6798	Discontinued
0.7566	Intermediate Similarity	NPD3764	Approved
0.7562	Intermediate Similarity	NPD6799	Approved
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD17	Approved
0.7534	Intermediate Similarity	NPD1778	Approved
0.7529	Intermediate Similarity	NPD6765	Approved
0.7529	Intermediate Similarity	NPD6764	Approved
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6004	Phase 3
0.7516	Intermediate Similarity	NPD6005	Phase 3
0.7516	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6002	Phase 3
0.7515	Intermediate Similarity	NPD1934	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD7497	Discontinued
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD7095	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.7485	Intermediate Similarity	NPD7239	Suspended
0.7468	Intermediate Similarity	NPD2979	Phase 3
0.7467	Intermediate Similarity	NPD2797	Approved
0.7457	Intermediate Similarity	NPD7054	Approved
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4476	Approved
0.7452	Intermediate Similarity	NPD4477	Approved
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3268	Approved
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7429	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD3817	Phase 2
0.7423	Intermediate Similarity	NPD7427	Discontinued
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7414	Intermediate Similarity	NPD7472	Approved
0.7405	Intermediate Similarity	NPD5763	Approved
0.7405	Intermediate Similarity	NPD5762	Approved
0.7397	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD1510	Phase 2
0.7375	Intermediate Similarity	NPD4110	Phase 3
0.7375	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.736	Intermediate Similarity	NPD6784	Approved
0.736	Intermediate Similarity	NPD6785	Approved
0.7355	Intermediate Similarity	NPD4307	Phase 2
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7349	Intermediate Similarity	NPD6677	Suspended
0.7347	Intermediate Similarity	NPD5691	Approved
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5404	Approved
0.7342	Intermediate Similarity	NPD5405	Approved
0.7342	Intermediate Similarity	NPD5406	Approved
0.7342	Intermediate Similarity	NPD1551	Phase 2
0.7342	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7251	Discontinued
0.733	Intermediate Similarity	NPD7685	Pre-registration
0.7321	Intermediate Similarity	NPD5402	Approved
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7317	Intermediate Similarity	NPD920	Approved
0.7317	Intermediate Similarity	NPD5403	Approved
0.7315	Intermediate Similarity	NPD1281	Approved
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2800	Approved
0.7312	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6674	Discontinued
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD5735	Approved
0.7305	Intermediate Similarity	NPD7577	Discontinued
0.7305	Intermediate Similarity	NPD37	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.7301	Intermediate Similarity	NPD5401	Approved
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7297	Intermediate Similarity	NPD4626	Approved
0.729	Intermediate Similarity	NPD6233	Phase 2
0.729	Intermediate Similarity	NPD6663	Approved
0.7288	Intermediate Similarity	NPD7808	Phase 3
0.7285	Intermediate Similarity	NPD8651	Approved
0.7284	Intermediate Similarity	NPD7440	Discontinued
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD4965	Approved
0.7273	Intermediate Similarity	NPD7008	Discontinued
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7261	Intermediate Similarity	NPD1607	Approved
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7255	Intermediate Similarity	NPD5736	Approved
0.7244	Intermediate Similarity	NPD1240	Approved
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7237	Intermediate Similarity	NPD3267	Approved
0.7237	Intermediate Similarity	NPD3266	Approved
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7233	Intermediate Similarity	NPD2438	Suspended
0.723	Intermediate Similarity	NPD5585	Approved
0.7226	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3887	Approved
0.7219	Intermediate Similarity	NPD5327	Phase 3
0.7205	Intermediate Similarity	NPD1243	Approved
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.72	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.7195	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7874	Approved
0.7188	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD6666	Approved
0.7178	Intermediate Similarity	NPD6667	Approved
0.7178	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3225	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