NPASS Compound

Structure

NPC127917 OpenBabel07101718282D 33 35 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 0.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4373 -1.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 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 1.9049 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 15 20 1 0 0 0 0 16 27 2 0 0 0 0 16 30 1 0 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 14 1 6 0 0 0 19 22 1 0 0 0 0 20 30 1 6 0 0 0 21 13 1 6 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.28
Volume:	483.568
LogP:	3.789
LogD:	2.623
LogS:	-3.887
# Rotatable Bonds:	7
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	6.012
Fsp3:	0.808
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:	-4.849
MDCK Permeability:	4.693773735198192e-05
Pgp-inhibitor:	0.888
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.196

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	73.2688217163086%
Volume Distribution (VD):	1.898
Pgp-substrate:	19.37253761291504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.367
CYP3A4-substrate:	0.568

ADMET: Excretion

Clearance (CL):	3.352
Half-life (T1/2):	0.469

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.286
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.179
Carcinogencity:	0.195
Eye Corrosion:	0.035
Eye Irritation:	0.034
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC127917

Natural Product ID:	NPC127917
*Common Name:**	Palmonine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZGFSWJUYGOEFE-LBMCJUAKSA-N
Standard InCHI:	InChI=1S/C26H40O7/c1-14(2)19-9-11-25(7,32-17(5)28)23-21-13-15(3)20(30-16(4)27)10-12-26(8,33-18(6)29)24(31-21)22(19)23/h14,19-24H,3,9-13H2,1-2,4-8H3/t19-,20+,21-,22-,23-,24-,25-,26-/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@@](C)(OC(=O)C)[C@@H]2O[C@H](CC1=C)[C@@H]1[C@H]2[C@H](CC[C@@]1(C)OC(=O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471887
PubChem CID:	44559757
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane diterpenoids

*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
NPO12665	Eunicella verrucosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687472]
NPO12665	Eunicella verrucosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853007]
NPO12665	Eunicella verrucosa	Species	Gorgoniidae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.0	ug ml-1	PMID[476351]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[476351]

☑ 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 NPC127917 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	195
0.1-0.2	1929
0.2-0.3	5964
0.3-0.4	14848
0.4-0.5	8522
0.5-0.6	8222
0.6-0.7	2753
0.7-0.8	224
0.8-0.85	17
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC264610
0.9259	High Similarity	NPC476725
0.9146	High Similarity	NPC475684
0.9036	High Similarity	NPC44538
0.8929	High Similarity	NPC92370
0.8929	High Similarity	NPC476723
0.8929	High Similarity	NPC75443
0.8929	High Similarity	NPC470260
0.8929	High Similarity	NPC476724
0.8889	High Similarity	NPC103171
0.8837	High Similarity	NPC122057
0.8824	High Similarity	NPC291875
0.8824	High Similarity	NPC161560
0.8795	High Similarity	NPC196911
0.8795	High Similarity	NPC471379
0.878	High Similarity	NPC5958
0.869	High Similarity	NPC214315
0.8621	High Similarity	NPC8729
0.8621	High Similarity	NPC91251
0.8621	High Similarity	NPC312805
0.8537	High Similarity	NPC118116
0.8537	High Similarity	NPC77003
0.8506	High Similarity	NPC471378
0.8506	High Similarity	NPC312471
0.8409	Intermediate Similarity	NPC165180
0.8333	Intermediate Similarity	NPC239308
0.8333	Intermediate Similarity	NPC476720
0.8228	Intermediate Similarity	NPC476718
0.8222	Intermediate Similarity	NPC476722
0.8046	Intermediate Similarity	NPC322922
0.8046	Intermediate Similarity	NPC321812
0.8025	Intermediate Similarity	NPC36479
0.8022	Intermediate Similarity	NPC476716
0.7979	Intermediate Similarity	NPC272223
0.7957	Intermediate Similarity	NPC473244
0.7957	Intermediate Similarity	NPC111348
0.7927	Intermediate Similarity	NPC136424
0.7927	Intermediate Similarity	NPC293223
0.7889	Intermediate Similarity	NPC475776
0.7865	Intermediate Similarity	NPC309656
0.7841	Intermediate Similarity	NPC102996
0.7831	Intermediate Similarity	NPC476719
0.7802	Intermediate Similarity	NPC41838
0.7778	Intermediate Similarity	NPC123122
0.7778	Intermediate Similarity	NPC246028
0.7753	Intermediate Similarity	NPC175293
0.7753	Intermediate Similarity	NPC102640
0.7742	Intermediate Similarity	NPC471362
0.7742	Intermediate Similarity	NPC471372
0.7742	Intermediate Similarity	NPC472189
0.7738	Intermediate Similarity	NPC43463
0.7738	Intermediate Similarity	NPC191345
0.7738	Intermediate Similarity	NPC252483
0.7711	Intermediate Similarity	NPC329626
0.7708	Intermediate Similarity	NPC472554
0.7674	Intermediate Similarity	NPC25554
0.7667	Intermediate Similarity	NPC106332
0.7667	Intermediate Similarity	NPC69713
0.766	Intermediate Similarity	NPC473964
0.766	Intermediate Similarity	NPC284194
0.766	Intermediate Similarity	NPC211810
0.766	Intermediate Similarity	NPC171598
0.766	Intermediate Similarity	NPC471765
0.766	Intermediate Similarity	NPC221801
0.7634	Intermediate Similarity	NPC471446
0.7634	Intermediate Similarity	NPC3359
0.7634	Intermediate Similarity	NPC66581
0.7634	Intermediate Similarity	NPC474841
0.7634	Intermediate Similarity	NPC473434
0.7634	Intermediate Similarity	NPC140277
0.7634	Intermediate Similarity	NPC472360
0.7634	Intermediate Similarity	NPC472416
0.7629	Intermediate Similarity	NPC472552
0.7609	Intermediate Similarity	NPC208839
0.7609	Intermediate Similarity	NPC130840
0.7604	Intermediate Similarity	NPC38855
0.7604	Intermediate Similarity	NPC188968
0.7582	Intermediate Similarity	NPC261320
0.7579	Intermediate Similarity	NPC473963
0.7579	Intermediate Similarity	NPC472188
0.7579	Intermediate Similarity	NPC274793
0.7579	Intermediate Similarity	NPC474921
0.7579	Intermediate Similarity	NPC472998
0.7576	Intermediate Similarity	NPC470263
0.7558	Intermediate Similarity	NPC186594
0.7558	Intermediate Similarity	NPC469802
0.7558	Intermediate Similarity	NPC474739
0.7556	Intermediate Similarity	NPC166857
0.7556	Intermediate Similarity	NPC475087
0.7553	Intermediate Similarity	NPC157686
0.7553	Intermediate Similarity	NPC259042
0.7553	Intermediate Similarity	NPC276110
0.7551	Intermediate Similarity	NPC61442
0.7527	Intermediate Similarity	NPC7349
0.7527	Intermediate Similarity	NPC163902
0.7526	Intermediate Similarity	NPC475617
0.7526	Intermediate Similarity	NPC49532
0.75	Intermediate Similarity	NPC318917
0.75	Intermediate Similarity	NPC471366
0.75	Intermediate Similarity	NPC220216
0.75	Intermediate Similarity	NPC476800
0.75	Intermediate Similarity	NPC472186
0.7475	Intermediate Similarity	NPC473543
0.7474	Intermediate Similarity	NPC194132
0.7474	Intermediate Similarity	NPC93245
0.7474	Intermediate Similarity	NPC8954
0.7474	Intermediate Similarity	NPC209297
0.7474	Intermediate Similarity	NPC475380
0.7474	Intermediate Similarity	NPC284518
0.7474	Intermediate Similarity	NPC94905
0.7474	Intermediate Similarity	NPC129569
0.7474	Intermediate Similarity	NPC475304
0.7473	Intermediate Similarity	NPC93411
0.7471	Intermediate Similarity	NPC116320
0.7471	Intermediate Similarity	NPC119922
0.7471	Intermediate Similarity	NPC211049
0.7449	Intermediate Similarity	NPC177701
0.7449	Intermediate Similarity	NPC470972
0.7449	Intermediate Similarity	NPC11956
0.7449	Intermediate Similarity	NPC476471
0.7449	Intermediate Similarity	NPC475344
0.7447	Intermediate Similarity	NPC161998
0.7447	Intermediate Similarity	NPC469596
0.7447	Intermediate Similarity	NPC148000
0.7447	Intermediate Similarity	NPC182826
0.7447	Intermediate Similarity	NPC105375
0.7447	Intermediate Similarity	NPC225474
0.7447	Intermediate Similarity	NPC105490
0.7426	Intermediate Similarity	NPC38948
0.7423	Intermediate Similarity	NPC473545
0.7423	Intermediate Similarity	NPC472187
0.7423	Intermediate Similarity	NPC473204
0.7419	Intermediate Similarity	NPC124374
0.7419	Intermediate Similarity	NPC219516
0.7416	Intermediate Similarity	NPC471367
0.7416	Intermediate Similarity	NPC470011
0.7416	Intermediate Similarity	NPC299963
0.7396	Intermediate Similarity	NPC254121
0.7396	Intermediate Similarity	NPC100912
0.7396	Intermediate Similarity	NPC475446
0.7396	Intermediate Similarity	NPC113976
0.7396	Intermediate Similarity	NPC198549
0.7396	Intermediate Similarity	NPC311241
0.7386	Intermediate Similarity	NPC216800
0.7374	Intermediate Similarity	NPC473523
0.7374	Intermediate Similarity	NPC120009
0.7374	Intermediate Similarity	NPC474124
0.7374	Intermediate Similarity	NPC23584
0.7374	Intermediate Similarity	NPC99510
0.7368	Intermediate Similarity	NPC241047
0.7368	Intermediate Similarity	NPC56369
0.7368	Intermediate Similarity	NPC469583
0.7363	Intermediate Similarity	NPC471779
0.7356	Intermediate Similarity	NPC233332
0.7356	Intermediate Similarity	NPC76054
0.7353	Intermediate Similarity	NPC206618
0.7347	Intermediate Similarity	NPC11974
0.7347	Intermediate Similarity	NPC308824
0.734	Intermediate Similarity	NPC99653
0.734	Intermediate Similarity	NPC12297
0.734	Intermediate Similarity	NPC26046
0.7333	Intermediate Similarity	NPC164424
0.7333	Intermediate Similarity	NPC35933
0.7327	Intermediate Similarity	NPC475587
0.7327	Intermediate Similarity	NPC475510
0.732	Intermediate Similarity	NPC107806
0.732	Intermediate Similarity	NPC72647
0.7312	Intermediate Similarity	NPC123252
0.7312	Intermediate Similarity	NPC209816
0.7312	Intermediate Similarity	NPC219937
0.7312	Intermediate Similarity	NPC10274
0.7312	Intermediate Similarity	NPC194485
0.7312	Intermediate Similarity	NPC153853
0.7312	Intermediate Similarity	NPC53890
0.7303	Intermediate Similarity	NPC49208
0.7303	Intermediate Similarity	NPC476721
0.7303	Intermediate Similarity	NPC473742
0.7303	Intermediate Similarity	NPC470261
0.73	Intermediate Similarity	NPC477127
0.73	Intermediate Similarity	NPC473577
0.73	Intermediate Similarity	NPC475585
0.73	Intermediate Similarity	NPC474550
0.7292	Intermediate Similarity	NPC169270
0.7292	Intermediate Similarity	NPC292718
0.7292	Intermediate Similarity	NPC472996
0.7292	Intermediate Similarity	NPC472997
0.7292	Intermediate Similarity	NPC111834
0.7292	Intermediate Similarity	NPC306797
0.7292	Intermediate Similarity	NPC472995
0.7283	Intermediate Similarity	NPC160304
0.7273	Intermediate Similarity	NPC238397
0.7273	Intermediate Similarity	NPC471363
0.7263	Intermediate Similarity	NPC39453
0.7263	Intermediate Similarity	NPC96736
0.7263	Intermediate Similarity	NPC24861
0.7263	Intermediate Similarity	NPC178949
0.7262	Intermediate Similarity	NPC71152
0.7255	Intermediate Similarity	NPC48548
0.7255	Intermediate Similarity	NPC473939
0.7255	Intermediate Similarity	NPC473517

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 NPC127917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	2482
0.2-0.3	3914
0.3-0.4	1808
0.4-0.5	455
0.5-0.6	263
0.6-0.7	33
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7245	Intermediate Similarity	NPD6648	Approved
0.7172	Intermediate Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD4225	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1145	Discontinued
0.6606	Remote Similarity	NPD8133	Approved
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7328	Approved
0.6518	Remote Similarity	NPD7327	Approved
0.6495	Remote Similarity	NPD6051	Approved
0.6491	Remote Similarity	NPD8033	Approved
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7516	Approved
0.6429	Remote Similarity	NPD3168	Discontinued
0.6429	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD46	Approved
0.6421	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD8294	Approved
0.6404	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6348	Remote Similarity	NPD8296	Approved
0.6348	Remote Similarity	NPD8380	Approved
0.6348	Remote Similarity	NPD8379	Approved
0.6348	Remote Similarity	NPD8335	Approved
0.6348	Remote Similarity	NPD8378	Approved
0.6327	Remote Similarity	NPD1695	Approved
0.6296	Remote Similarity	NPD6686	Approved
0.6286	Remote Similarity	NPD7632	Discontinued
0.6207	Remote Similarity	NPD7503	Approved
0.6204	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7115	Discovery
0.6139	Remote Similarity	NPD6399	Phase 3
0.6134	Remote Similarity	NPD7507	Approved
0.6132	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7524	Approved
0.6105	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD1694	Approved
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7900	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6068	Remote Similarity	NPD8513	Phase 3
0.6068	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD8516	Approved
0.6068	Remote Similarity	NPD8515	Approved
0.6064	Remote Similarity	NPD7525	Registered
0.6042	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7319	Approved
0.5982	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5963	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6402	Approved
0.5963	Remote Similarity	NPD6675	Approved
0.5963	Remote Similarity	NPD5739	Approved
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.5955	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD2686	Approved
0.5955	Remote Similarity	NPD2687	Approved
0.5955	Remote Similarity	NPD2254	Approved
0.5946	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6921	Approved
0.593	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD7748	Approved
0.5917	Remote Similarity	NPD7492	Approved
0.5905	Remote Similarity	NPD7902	Approved
0.5893	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD7983	Approved
0.5877	Remote Similarity	NPD4632	Approved
0.5876	Remote Similarity	NPD3669	Approved
0.5876	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6616	Approved
0.5865	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5330	Approved
0.5859	Remote Similarity	NPD6684	Approved
0.5859	Remote Similarity	NPD7521	Approved
0.5859	Remote Similarity	NPD6409	Approved
0.5859	Remote Similarity	NPD7146	Approved
0.5859	Remote Similarity	NPD4249	Approved
0.5859	Remote Similarity	NPD7334	Approved
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5847	Remote Similarity	NPD6319	Approved
0.5847	Remote Similarity	NPD6054	Approved
0.5847	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD1780	Approved
0.5833	Remote Similarity	NPD1779	Approved
0.582	Remote Similarity	NPD8293	Discontinued
0.582	Remote Similarity	NPD7078	Approved
0.582	Remote Similarity	NPD8074	Phase 3
0.5818	Remote Similarity	NPD5357	Phase 1
0.5814	Remote Similarity	NPD371	Approved
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.58	Remote Similarity	NPD7750	Discontinued
0.5789	Remote Similarity	NPD7645	Phase 2
0.5772	Remote Similarity	NPD7736	Approved
0.5766	Remote Similarity	NPD6412	Phase 2
0.5766	Remote Similarity	NPD5697	Approved
0.5766	Remote Similarity	NPD5701	Approved
0.5758	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD7290	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD6370	Approved
0.5743	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6672	Approved
0.5743	Remote Similarity	NPD6903	Approved
0.5743	Remote Similarity	NPD5737	Approved
0.5729	Remote Similarity	NPD6931	Approved
0.5729	Remote Similarity	NPD4820	Approved
0.5729	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4822	Approved
0.5729	Remote Similarity	NPD4819	Approved
0.5729	Remote Similarity	NPD6930	Phase 2
0.5729	Remote Similarity	NPD4821	Approved
0.5728	Remote Similarity	NPD7515	Phase 2
0.5728	Remote Similarity	NPD5693	Phase 1
0.5726	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6009	Approved
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5686	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6101	Approved
0.5684	Remote Similarity	NPD6115	Approved
0.5684	Remote Similarity	NPD6118	Approved
0.5684	Remote Similarity	NPD6697	Approved
0.5684	Remote Similarity	NPD6114	Approved
0.5667	Remote Similarity	NPD6016	Approved
0.5667	Remote Similarity	NPD6015	Approved
0.5667	Remote Similarity	NPD5983	Phase 2
0.5664	Remote Similarity	NPD6012	Approved
0.5664	Remote Similarity	NPD6013	Approved
0.5664	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6882	Approved
0.5644	Remote Similarity	NPD3573	Approved
0.5625	Remote Similarity	NPD6929	Approved
0.562	Remote Similarity	NPD5988	Approved
0.5619	Remote Similarity	NPD5282	Discontinued
0.561	Remote Similarity	NPD6336	Discontinued
0.5607	Remote Similarity	NPD6083	Phase 2
0.5607	Remote Similarity	NPD6084	Phase 2

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