NPASS Compound

Structure

CID63514 OpenBabel06191715402D 40 45 0 0 1 0 0 0 0 0999 V2000 0.2569 2.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 2.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9439 0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 0.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5325 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1512 1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6307 1.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4214 1.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 0.7832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2172 0.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7493 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 0.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7831 -1.2740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2528 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5128 0.8416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4214 1.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5580 0.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7831 -0.7185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6496 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5499 -0.9524 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5120 0.1168 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5499 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6496 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5499 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7493 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1325 0.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4563 0.1504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5499 -0.3175 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8536 1.0905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 -2.0531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3197 -0.3985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 0.0000 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 1.0100 0.7918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 34 2 0 0 0 0 19 14 1 1 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 22 33 1 0 0 0 0 23 31 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 29 37 2 0 0 0 0 30 38 1 0 0 0 0 31 40 1 0 0 0 0 32 33 1 1 0 0 0 32 40 1 0 0 0 0 33 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.26
Volume:	565.789
LogP:	6.182
LogD:	4.091
LogS:	-3.626
# Rotatable Bonds:	5
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	6.681
Fsp3:	0.545
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	1.609333230589982e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.2
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.339

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	98.3388900756836%
Volume Distribution (VD):	2.044
Pgp-substrate:	2.472532272338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	3.476
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.115
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC63514

Natural Product ID:	NPC63514
*Common Name:**	ORNMPVMTDJIPQS-NXABCWRFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ORNMPVMTDJIPQS-NXABCWRFSA-N
Standard InCHI:	InChI=1S/C33H38O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,16,19,22-23,35H,9,13-15H2,1-7H3/b18-10+/t19-,22?,23?,32+,33-/m0/s1
SMILES:	O=C/C(=C/C[C@@]12OC(C3[C@@]42Oc2c(CC=C(C)C)c5OC(C)(C)C=Cc5c(c2C(=O)C4C[C@H](C1=O)C3)O)(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3809753
PubChem CID:	16078255
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:0003521] Pyranoxanthones

*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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13824	Thladiantha cordifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13824	Thladiantha cordifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13824	Thladiantha cordifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13824	Thladiantha cordifolia	Species	Cucurbitaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	6.0	mm	PMID[520633]

☑ 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 NPC63514 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	435
0.1-0.2	1598
0.2-0.3	3233
0.3-0.4	7221
0.4-0.5	10745
0.5-0.6	6326
0.6-0.7	6002
0.7-0.8	6893
0.8-0.85	176
0.85-0.9	35
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9568	High Similarity	NPC476196
0.9565	High Similarity	NPC223413
0.95	High Similarity	NPC131578
0.9398	High Similarity	NPC476199
0.9398	High Similarity	NPC476210
0.939	High Similarity	NPC476159
0.9387	High Similarity	NPC476146
0.9387	High Similarity	NPC40089
0.9387	High Similarity	NPC158329
0.9333	High Similarity	NPC476152
0.9313	High Similarity	NPC286422
0.9268	High Similarity	NPC55422
0.9268	High Similarity	NPC41598
0.9268	High Similarity	NPC75141
0.9268	High Similarity	NPC47634
0.9264	High Similarity	NPC476255
0.9217	High Similarity	NPC476229
0.9217	High Similarity	NPC476311
0.9162	High Similarity	NPC475398
0.9157	High Similarity	NPC118128
0.9152	High Similarity	NPC102810
0.9152	High Similarity	NPC476216
0.9102	High Similarity	NPC476139
0.9091	High Similarity	NPC193222
0.9085	High Similarity	NPC189689
0.908	High Similarity	NPC94796
0.9048	High Similarity	NPC162248
0.9042	High Similarity	NPC169018
0.903	High Similarity	NPC62444
0.903	High Similarity	NPC476056
0.9	High Similarity	NPC473729
0.8957	High Similarity	NPC475107
0.8957	High Similarity	NPC43490
0.8909	High Similarity	NPC476931
0.8889	High Similarity	NPC473607
0.8882	High Similarity	NPC227275
0.8882	High Similarity	NPC98943
0.8876	High Similarity	NPC475080
0.8875	High Similarity	NPC476162
0.883	High Similarity	NPC233978
0.8817	High Similarity	NPC477529
0.8788	High Similarity	NPC476929
0.8735	High Similarity	NPC475106
0.8698	High Similarity	NPC20734
0.8679	High Similarity	NPC82534
0.8667	High Similarity	NPC125969
0.8655	High Similarity	NPC469393
0.8606	High Similarity	NPC476930
0.8598	High Similarity	NPC476169
0.8588	High Similarity	NPC54903
0.8588	High Similarity	NPC286074
0.858	High Similarity	NPC475109
0.858	High Similarity	NPC17274
0.858	High Similarity	NPC85047
0.858	High Similarity	NPC120857
0.8571	High Similarity	NPC469395
0.8563	High Similarity	NPC61382
0.8563	High Similarity	NPC103816
0.8563	High Similarity	NPC104682
0.8553	High Similarity	NPC5990
0.8547	High Similarity	NPC17105
0.8547	High Similarity	NPC474276
0.8547	High Similarity	NPC147363
0.8547	High Similarity	NPC73899
0.8537	High Similarity	NPC236756
0.8537	High Similarity	NPC209760
0.8537	High Similarity	NPC311579
0.8537	High Similarity	NPC100134
0.8529	High Similarity	NPC150131
0.8512	High Similarity	NPC219861
0.8512	High Similarity	NPC193998
0.8503	High Similarity	NPC172687
0.8503	High Similarity	NPC121647
0.8494	Intermediate Similarity	NPC272196
0.8476	Intermediate Similarity	NPC210597
0.8476	Intermediate Similarity	NPC477957
0.8476	Intermediate Similarity	NPC288534
0.8471	Intermediate Similarity	NPC469394
0.8471	Intermediate Similarity	NPC82330
0.8466	Intermediate Similarity	NPC471115
0.8466	Intermediate Similarity	NPC476509
0.8466	Intermediate Similarity	NPC29777
0.8462	Intermediate Similarity	NPC473009
0.8462	Intermediate Similarity	NPC472581
0.8452	Intermediate Similarity	NPC472346
0.8448	Intermediate Similarity	NPC478050
0.8443	Intermediate Similarity	NPC264932
0.8443	Intermediate Similarity	NPC311574
0.8434	Intermediate Similarity	NPC146636
0.8434	Intermediate Similarity	NPC192587
0.8434	Intermediate Similarity	NPC164427
0.843	Intermediate Similarity	NPC193698
0.843	Intermediate Similarity	NPC313717
0.843	Intermediate Similarity	NPC315306
0.8424	Intermediate Similarity	NPC248793
0.8424	Intermediate Similarity	NPC180301
0.8421	Intermediate Similarity	NPC292233
0.8415	Intermediate Similarity	NPC472580
0.8415	Intermediate Similarity	NPC305965
0.8415	Intermediate Similarity	NPC178484
0.8415	Intermediate Similarity	NPC471229
0.8412	Intermediate Similarity	NPC136641
0.8412	Intermediate Similarity	NPC316262
0.8412	Intermediate Similarity	NPC473908
0.8412	Intermediate Similarity	NPC314653
0.8412	Intermediate Similarity	NPC473010
0.8405	Intermediate Similarity	NPC214493
0.8402	Intermediate Similarity	NPC474150
0.8402	Intermediate Similarity	NPC472402
0.8402	Intermediate Similarity	NPC473012
0.8402	Intermediate Similarity	NPC474162
0.8395	Intermediate Similarity	NPC245757
0.8395	Intermediate Similarity	NPC304351
0.8393	Intermediate Similarity	NPC195136
0.8393	Intermediate Similarity	NPC470810
0.8393	Intermediate Similarity	NPC472618
0.8383	Intermediate Similarity	NPC161650
0.8383	Intermediate Similarity	NPC281137
0.8383	Intermediate Similarity	NPC65504
0.8383	Intermediate Similarity	NPC282390
0.8383	Intermediate Similarity	NPC210048
0.8383	Intermediate Similarity	NPC201127
0.8373	Intermediate Similarity	NPC217706
0.8373	Intermediate Similarity	NPC471116
0.8373	Intermediate Similarity	NPC259710
0.8373	Intermediate Similarity	NPC275575
0.8373	Intermediate Similarity	NPC207809
0.8373	Intermediate Similarity	NPC304207
0.8373	Intermediate Similarity	NPC48579
0.8372	Intermediate Similarity	NPC152477
0.8372	Intermediate Similarity	NPC288813
0.8365	Intermediate Similarity	NPC469818
0.8364	Intermediate Similarity	NPC473996
0.8364	Intermediate Similarity	NPC476238
0.8364	Intermediate Similarity	NPC142527
0.8364	Intermediate Similarity	NPC285623
0.8364	Intermediate Similarity	NPC31627
0.8364	Intermediate Similarity	NPC327269
0.8363	Intermediate Similarity	NPC125465
0.8363	Intermediate Similarity	NPC272502
0.8363	Intermediate Similarity	NPC120593
0.8363	Intermediate Similarity	NPC235610
0.8354	Intermediate Similarity	NPC267117
0.8353	Intermediate Similarity	NPC100849
0.8353	Intermediate Similarity	NPC109180
0.8353	Intermediate Similarity	NPC12461
0.8352	Intermediate Similarity	NPC244903
0.8344	Intermediate Similarity	NPC160821
0.8344	Intermediate Similarity	NPC39195
0.8344	Intermediate Similarity	NPC132592
0.8344	Intermediate Similarity	NPC296869
0.8344	Intermediate Similarity	NPC266572
0.8344	Intermediate Similarity	NPC145467
0.8343	Intermediate Similarity	NPC301256
0.8343	Intermediate Similarity	NPC312273
0.8343	Intermediate Similarity	NPC478134
0.8333	Intermediate Similarity	NPC15815
0.8333	Intermediate Similarity	NPC477955
0.8333	Intermediate Similarity	NPC105584
0.8333	Intermediate Similarity	NPC2416
0.8333	Intermediate Similarity	NPC473135
0.8333	Intermediate Similarity	NPC470676
0.8333	Intermediate Similarity	NPC295090
0.8333	Intermediate Similarity	NPC472617
0.8333	Intermediate Similarity	NPC476153
0.8333	Intermediate Similarity	NPC215885
0.8333	Intermediate Similarity	NPC473132
0.8333	Intermediate Similarity	NPC204879
0.8324	Intermediate Similarity	NPC131866
0.8324	Intermediate Similarity	NPC279209
0.8324	Intermediate Similarity	NPC102277
0.8323	Intermediate Similarity	NPC56049
0.8323	Intermediate Similarity	NPC54830
0.8323	Intermediate Similarity	NPC215917
0.8323	Intermediate Similarity	NPC10754
0.8323	Intermediate Similarity	NPC470352
0.8323	Intermediate Similarity	NPC20530
0.8315	Intermediate Similarity	NPC106700
0.8314	Intermediate Similarity	NPC476306
0.8314	Intermediate Similarity	NPC476459
0.8314	Intermediate Similarity	NPC241820
0.8314	Intermediate Similarity	NPC472622
0.8314	Intermediate Similarity	NPC260266
0.8314	Intermediate Similarity	NPC8965
0.8314	Intermediate Similarity	NPC218226
0.8313	Intermediate Similarity	NPC88983
0.8313	Intermediate Similarity	NPC472583
0.8313	Intermediate Similarity	NPC121568
0.8313	Intermediate Similarity	NPC329844
0.8313	Intermediate Similarity	NPC203080
0.8313	Intermediate Similarity	NPC469405
0.8313	Intermediate Similarity	NPC208806
0.8313	Intermediate Similarity	NPC7989
0.8313	Intermediate Similarity	NPC293286
0.8313	Intermediate Similarity	NPC210942
0.8313	Intermediate Similarity	NPC223701
0.8313	Intermediate Similarity	NPC169990
0.8313	Intermediate Similarity	NPC214632
0.8305	Intermediate Similarity	NPC208069
0.8304	Intermediate Similarity	NPC303174

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 NPC63514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	944
0.2-0.3	1860
0.3-0.4	2704
0.4-0.5	2030
0.5-0.6	840
0.6-0.7	270
0.7-0.8	121
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8214	Intermediate Similarity	NPD3882	Suspended
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8092	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7411	Suspended
0.807	Intermediate Similarity	NPD5494	Approved
0.8024	Intermediate Similarity	NPD4380	Phase 2
0.8023	Intermediate Similarity	NPD1247	Approved
0.7989	Intermediate Similarity	NPD6166	Phase 2
0.7989	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2532	Approved
0.7939	Intermediate Similarity	NPD2533	Approved
0.7939	Intermediate Similarity	NPD2534	Approved
0.7929	Intermediate Similarity	NPD6801	Discontinued
0.7919	Intermediate Similarity	NPD6959	Discontinued
0.7877	Intermediate Similarity	NPD7808	Phase 3
0.7853	Intermediate Similarity	NPD2800	Approved
0.7849	Intermediate Similarity	NPD3749	Approved
0.7841	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD1934	Approved
0.7821	Intermediate Similarity	NPD7251	Discontinued
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7803	Intermediate Similarity	NPD919	Approved
0.7802	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD2801	Approved
0.7771	Intermediate Similarity	NPD6799	Approved
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7746	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3817	Phase 2
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6559	Discontinued
0.7716	Intermediate Similarity	NPD1510	Phase 2
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7679	Intermediate Similarity	NPD1512	Approved
0.767	Intermediate Similarity	NPD6232	Discontinued
0.7669	Intermediate Similarity	NPD2796	Approved
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7654	Intermediate Similarity	NPD7054	Approved
0.7611	Intermediate Similarity	NPD7074	Phase 3
0.7611	Intermediate Similarity	NPD7472	Approved
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1511	Approved
0.7554	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD5402	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD3750	Approved
0.7485	Intermediate Similarity	NPD6651	Approved
0.7472	Intermediate Similarity	NPD5710	Approved
0.7472	Intermediate Similarity	NPD5711	Approved
0.747	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1240	Approved
0.7455	Intermediate Similarity	NPD6099	Approved
0.7455	Intermediate Similarity	NPD6100	Approved
0.7446	Intermediate Similarity	NPD8313	Approved
0.7446	Intermediate Similarity	NPD8312	Approved
0.7442	Intermediate Similarity	NPD3226	Approved
0.743	Intermediate Similarity	NPD3926	Phase 2
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5401	Approved
0.7396	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2403	Approved
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3787	Discontinued
0.7371	Intermediate Similarity	NPD5761	Phase 2
0.7371	Intermediate Similarity	NPD5760	Phase 2
0.7358	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7698	Approved
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7296	Intermediate Similarity	NPD7871	Phase 2
0.7296	Intermediate Similarity	NPD7870	Phase 2
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1243	Approved
0.7212	Intermediate Similarity	NPD5124	Phase 1
0.7212	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2344	Approved
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7186	Intermediate Similarity	NPD7701	Phase 2
0.7186	Intermediate Similarity	NPD3748	Approved
0.7186	Intermediate Similarity	NPD2799	Discontinued
0.7175	Intermediate Similarity	NPD1465	Phase 2
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.7164	Intermediate Similarity	NPD7801	Approved
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7128	Intermediate Similarity	NPD8285	Discontinued
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7121	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD7228	Approved
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.7098	Intermediate Similarity	NPD6534	Approved
0.7098	Intermediate Similarity	NPD6535	Approved
0.7097	Intermediate Similarity	NPD5953	Discontinued
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7076	Intermediate Similarity	NPD4628	Phase 3
0.7076	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4287	Approved
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2935	Discontinued
0.7035	Intermediate Similarity	NPD2309	Approved
0.7033	Intermediate Similarity	NPD7199	Phase 2
0.703	Intermediate Similarity	NPD2313	Discontinued
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD37	Approved
0.7019	Intermediate Similarity	NPD7907	Approved
0.7017	Intermediate Similarity	NPD6234	Discontinued
0.7011	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4360	Phase 2
0.701	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.7	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4361	Phase 2
0.6968	Remote Similarity	NPD6764	Approved
0.6968	Remote Similarity	NPD6765	Approved
0.6946	Remote Similarity	NPD943	Approved
0.6938	Remote Similarity	NPD8366	Approved
0.6935	Remote Similarity	NPD6823	Phase 2
0.6928	Remote Similarity	NPD3268	Approved
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7584	Approved
0.6879	Remote Similarity	NPD7003	Approved
0.6878	Remote Similarity	NPD7685	Pre-registration
0.6867	Remote Similarity	NPD4625	Phase 3
0.6857	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD5406	Approved
0.6842	Remote Similarity	NPD5404	Approved
0.6842	Remote Similarity	NPD4111	Phase 1
0.6842	Remote Similarity	NPD5408	Approved
0.6842	Remote Similarity	NPD5405	Approved
0.6842	Remote Similarity	NPD4665	Approved
0.6826	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3764	Approved
0.6823	Remote Similarity	NPD6784	Approved
0.6823	Remote Similarity	NPD6785	Approved
0.6808	Remote Similarity	NPD8491	Approved
0.68	Remote Similarity	NPD2493	Approved
0.68	Remote Similarity	NPD2494	Approved
0.6796	Remote Similarity	NPD8455	Phase 2
0.679	Remote Similarity	NPD1610	Phase 2
0.6789	Remote Similarity	NPD7240	Approved
0.6788	Remote Similarity	NPD2798	Approved
0.6784	Remote Similarity	NPD7033	Discontinued
0.6782	Remote Similarity	NPD8166	Discontinued
0.6782	Remote Similarity	NPD4582	Approved
0.6782	Remote Similarity	NPD4583	Approved
0.678	Remote Similarity	NPD6273	Approved
0.6778	Remote Similarity	NPD5890	Approved
0.6778	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5889	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