NPASS Compound

Structure

CID53911 OpenBabel06191715392D 32 35 0 0 1 0 0 0 0 0999 V2000 1.4598 -5.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9983 -5.1980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2724 -3.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3725 2.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 -0.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2067 -3.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6354 -4.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8109 -2.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6867 1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 -0.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6850 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 -1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2143 0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 -5.0967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8435 -1.4594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6861 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5296 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2146 1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3717 -0.0010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3723 1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5294 0.4860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0808 1.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3714 -1.0010 0.0000 O 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 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 24 2 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 20 3 1 6 0 0 0 20 21 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 30 1 6 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 31 2 0 0 0 0 26 30 1 6 0 0 0 26 32 1 0 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	505.518
LogP:	7.286
LogD:	5.487
LogS:	-6.075
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	4.829
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.737
MDCK Permeability:	1.0874752661038656e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.782
Plasma Protein Binding (PPB):	98.0376205444336%
Volume Distribution (VD):	1.167
Pgp-substrate:	1.355882167816162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.314
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.357
CYP2C9-substrate:	0.67
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.842

ADMET: Excretion

Clearance (CL):	7.081
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.65
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.902
Carcinogencity:	0.449
Eye Corrosion:	0.804
Eye Irritation:	0.418
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC53911

Natural Product ID:	NPC53911
*Common Name:**	Cornusalterin K
IUPAC Name:	(1R,8R,9S,10R,13S,14R,17S)-1-hydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methylheptan-2-yl]-1,2,7,8,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Cornusalterin K
Standard InCHIKey:	FEAAYJYTVFABGY-UHNHVWPPSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)10-9-11-20(3)21-14-16-29(7)22-12-13-24-27(4,5)25(31)18-26(32)30(24,8)23(22)15-17-28(21,29)6/h13,19-23,26,32H,9-12,14-18H2,1-8H3/t20-,21-,22+,23-,26+,28-,29+,30+/m0/s1
SMILES:	CC(C)CCC[C@H](C)[C@@H]1CC[C@]2(C)[C@@H]3CC=C4C(C)(C)C(=O)C[C@H]([C@]4(C)[C@H]3CC[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668104
PubChem CID:	50994389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11680.0	nM	PMID[449365]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	12830.0	nM	PMID[449365]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	12360.0	nM	PMID[449365]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	12020.0	nM	PMID[449365]

☑ 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 NPC53911 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	169
0.1-0.2	1260
0.2-0.3	5428
0.3-0.4	13573
0.4-0.5	9061
0.5-0.6	5841
0.6-0.7	4746
0.7-0.8	2286
0.8-0.85	239
0.85-0.9	80
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC328313
0.9277	High Similarity	NPC221758
0.9277	High Similarity	NPC59453
0.9176	High Similarity	NPC475740
0.9157	High Similarity	NPC278648
0.9157	High Similarity	NPC476082
0.907	High Similarity	NPC328539
0.9059	High Similarity	NPC474778
0.9059	High Similarity	NPC474733
0.9059	High Similarity	NPC145879
0.9059	High Similarity	NPC474732
0.9059	High Similarity	NPC31564
0.9059	High Similarity	NPC51014
0.9036	High Similarity	NPC151519
0.8966	High Similarity	NPC474245
0.8966	High Similarity	NPC32830
0.8966	High Similarity	NPC186688
0.8966	High Similarity	NPC86319
0.8966	High Similarity	NPC1015
0.8966	High Similarity	NPC31985
0.8966	High Similarity	NPC275740
0.8953	High Similarity	NPC472481
0.8953	High Similarity	NPC472484
0.8953	High Similarity	NPC472482
0.8953	High Similarity	NPC58063
0.8941	High Similarity	NPC202868
0.8941	High Similarity	NPC469948
0.8913	High Similarity	NPC110149
0.8876	High Similarity	NPC477520
0.8864	High Similarity	NPC48010
0.8851	High Similarity	NPC143767
0.8851	High Similarity	NPC131470
0.8851	High Similarity	NPC471722
0.8851	High Similarity	NPC471724
0.8837	High Similarity	NPC20688
0.8837	High Similarity	NPC155011
0.8824	High Similarity	NPC85774
0.8824	High Similarity	NPC82902
0.8824	High Similarity	NPC214043
0.8764	High Similarity	NPC185936
0.8764	High Similarity	NPC168027
0.875	High Similarity	NPC26959
0.875	High Similarity	NPC268406
0.875	High Similarity	NPC69627
0.875	High Similarity	NPC76879
0.8736	High Similarity	NPC96496
0.8736	High Similarity	NPC474684
0.8736	High Similarity	NPC298904
0.8736	High Similarity	NPC57469
0.8736	High Similarity	NPC142361
0.8721	High Similarity	NPC470574
0.8721	High Similarity	NPC471224
0.8721	High Similarity	NPC474218
0.8696	High Similarity	NPC190554
0.869	High Similarity	NPC14151
0.8681	High Similarity	NPC472485
0.8667	High Similarity	NPC69454
0.8652	High Similarity	NPC183283
0.8636	High Similarity	NPC472483
0.8636	High Similarity	NPC193360
0.8621	High Similarity	NPC94755
0.8621	High Similarity	NPC222613
0.8621	High Similarity	NPC475022
0.8621	High Similarity	NPC72133
0.8621	High Similarity	NPC118648
0.8621	High Similarity	NPC469994
0.8621	High Similarity	NPC470955
0.8605	High Similarity	NPC472265
0.8605	High Similarity	NPC472480
0.8605	High Similarity	NPC473246
0.8571	High Similarity	NPC164999
0.8571	High Similarity	NPC166906
0.8571	High Similarity	NPC245972
0.8571	High Similarity	NPC196485
0.8556	High Similarity	NPC63748
0.8556	High Similarity	NPC272746
0.8539	High Similarity	NPC472477
0.8539	High Similarity	NPC472970
0.8539	High Similarity	NPC309603
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC477943
0.8539	High Similarity	NPC473999
0.8539	High Similarity	NPC119416
0.8539	High Similarity	NPC472971
0.8539	High Similarity	NPC472475
0.8539	High Similarity	NPC475921
0.8523	High Similarity	NPC90652
0.8523	High Similarity	NPC317590
0.8523	High Similarity	NPC159046
0.8523	High Similarity	NPC233836
0.8523	High Similarity	NPC187376
0.8511	High Similarity	NPC83709
0.8511	High Similarity	NPC15390
0.8506	High Similarity	NPC197823
0.8506	High Similarity	NPC474083
0.8478	Intermediate Similarity	NPC317586
0.8478	Intermediate Similarity	NPC259286
0.8478	Intermediate Similarity	NPC473170
0.8478	Intermediate Similarity	NPC470016
0.8478	Intermediate Similarity	NPC469599
0.8462	Intermediate Similarity	NPC475255
0.8462	Intermediate Similarity	NPC472930
0.8462	Intermediate Similarity	NPC12722
0.8462	Intermediate Similarity	NPC477855
0.8462	Intermediate Similarity	NPC474807
0.8444	Intermediate Similarity	NPC85173
0.8444	Intermediate Similarity	NPC191684
0.8444	Intermediate Similarity	NPC126993
0.8427	Intermediate Similarity	NPC474677
0.8427	Intermediate Similarity	NPC470417
0.8427	Intermediate Similarity	NPC242864
0.8409	Intermediate Similarity	NPC327115
0.8409	Intermediate Similarity	NPC473168
0.8409	Intermediate Similarity	NPC55309
0.8409	Intermediate Similarity	NPC89077
0.8409	Intermediate Similarity	NPC472491
0.8409	Intermediate Similarity	NPC472494
0.8409	Intermediate Similarity	NPC28252
0.8404	Intermediate Similarity	NPC114274
0.8391	Intermediate Similarity	NPC180834
0.8391	Intermediate Similarity	NPC329043
0.8391	Intermediate Similarity	NPC237712
0.8391	Intermediate Similarity	NPC33913
0.8391	Intermediate Similarity	NPC321187
0.8391	Intermediate Similarity	NPC161423
0.8391	Intermediate Similarity	NPC58841
0.8391	Intermediate Similarity	NPC227064
0.8387	Intermediate Similarity	NPC192428
0.8387	Intermediate Similarity	NPC471463
0.8387	Intermediate Similarity	NPC328162
0.8387	Intermediate Similarity	NPC249954
0.8387	Intermediate Similarity	NPC305483
0.8387	Intermediate Similarity	NPC96859
0.8387	Intermediate Similarity	NPC173272
0.8372	Intermediate Similarity	NPC110780
0.8372	Intermediate Similarity	NPC48362
0.837	Intermediate Similarity	NPC474529
0.837	Intermediate Similarity	NPC111015
0.837	Intermediate Similarity	NPC292793
0.8353	Intermediate Similarity	NPC2482
0.8353	Intermediate Similarity	NPC472478
0.8352	Intermediate Similarity	NPC473998
0.8352	Intermediate Similarity	NPC131872
0.8352	Intermediate Similarity	NPC189520
0.8352	Intermediate Similarity	NPC212301
0.8352	Intermediate Similarity	NPC86266
0.8352	Intermediate Similarity	NPC110657
0.8352	Intermediate Similarity	NPC475806
0.8333	Intermediate Similarity	NPC84271
0.8333	Intermediate Similarity	NPC102414
0.8333	Intermediate Similarity	NPC122116
0.8333	Intermediate Similarity	NPC185530
0.8333	Intermediate Similarity	NPC128496
0.8333	Intermediate Similarity	NPC77168
0.8333	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC82635
0.8333	Intermediate Similarity	NPC2983
0.8316	Intermediate Similarity	NPC477521
0.8315	Intermediate Similarity	NPC4643
0.8315	Intermediate Similarity	NPC93778
0.8315	Intermediate Similarity	NPC141292
0.8315	Intermediate Similarity	NPC73064
0.8315	Intermediate Similarity	NPC138756
0.8313	Intermediate Similarity	NPC240604
0.8313	Intermediate Similarity	NPC321016
0.8313	Intermediate Similarity	NPC107059
0.8313	Intermediate Similarity	NPC300324
0.8313	Intermediate Similarity	NPC321381
0.8298	Intermediate Similarity	NPC18509
0.8298	Intermediate Similarity	NPC108078
0.8295	Intermediate Similarity	NPC133954
0.828	Intermediate Similarity	NPC271195
0.828	Intermediate Similarity	NPC472932
0.828	Intermediate Similarity	NPC173875
0.828	Intermediate Similarity	NPC200702
0.828	Intermediate Similarity	NPC174948
0.828	Intermediate Similarity	NPC127063
0.828	Intermediate Similarity	NPC48330
0.828	Intermediate Similarity	NPC318282
0.828	Intermediate Similarity	NPC469995
0.8276	Intermediate Similarity	NPC475726
0.8276	Intermediate Similarity	NPC471036
0.8276	Intermediate Similarity	NPC291320
0.8276	Intermediate Similarity	NPC472743
0.8261	Intermediate Similarity	NPC170220
0.8261	Intermediate Similarity	NPC470224
0.8261	Intermediate Similarity	NPC474736
0.8261	Intermediate Similarity	NPC141497
0.8261	Intermediate Similarity	NPC470375
0.8261	Intermediate Similarity	NPC107674
0.8261	Intermediate Similarity	NPC206810
0.8261	Intermediate Similarity	NPC470376
0.8256	Intermediate Similarity	NPC147066
0.8247	Intermediate Similarity	NPC312900
0.8247	Intermediate Similarity	NPC26478
0.8247	Intermediate Similarity	NPC191892
0.8242	Intermediate Similarity	NPC180849
0.8242	Intermediate Similarity	NPC80401
0.8242	Intermediate Similarity	NPC69622
0.8242	Intermediate Similarity	NPC472476

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 NPC53911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1592
0.2-0.3	4174
0.3-0.4	2204
0.4-0.5	559
0.5-0.6	155
0.6-0.7	126
0.7-0.8	152
0.8-0.85	25
0.85-0.9	8
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9277	High Similarity	NPD4786	Approved
0.9186	High Similarity	NPD5328	Approved
0.9036	High Similarity	NPD3667	Approved
0.8977	High Similarity	NPD6079	Approved
0.8621	High Similarity	NPD3618	Phase 1
0.8391	Intermediate Similarity	NPD3133	Approved
0.8391	Intermediate Similarity	NPD3665	Phase 1
0.8391	Intermediate Similarity	NPD3666	Approved
0.8387	Intermediate Similarity	NPD5222	Approved
0.8387	Intermediate Similarity	NPD5221	Approved
0.8387	Intermediate Similarity	NPD4697	Phase 3
0.8387	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD4755	Approved
0.8298	Intermediate Similarity	NPD5173	Approved
0.8261	Intermediate Similarity	NPD6399	Phase 3
0.8261	Intermediate Similarity	NPD4202	Approved
0.8193	Intermediate Similarity	NPD6942	Approved
0.8193	Intermediate Similarity	NPD7339	Approved
0.8182	Intermediate Similarity	NPD3668	Phase 3
0.8125	Intermediate Similarity	NPD4700	Approved
0.8125	Intermediate Similarity	NPD5285	Approved
0.8125	Intermediate Similarity	NPD4696	Approved
0.8125	Intermediate Similarity	NPD5286	Approved
0.8041	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD5279	Phase 3
0.8	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5224	Approved
0.7959	Intermediate Similarity	NPD4633	Approved
0.7959	Intermediate Similarity	NPD5226	Approved
0.7959	Intermediate Similarity	NPD5225	Approved
0.7959	Intermediate Similarity	NPD5211	Phase 2
0.7955	Intermediate Similarity	NPD4223	Phase 3
0.7955	Intermediate Similarity	NPD4221	Approved
0.7935	Intermediate Similarity	NPD4753	Phase 2
0.79	Intermediate Similarity	NPD5739	Approved
0.79	Intermediate Similarity	NPD7128	Approved
0.79	Intermediate Similarity	NPD6675	Approved
0.79	Intermediate Similarity	NPD6402	Approved
0.7889	Intermediate Similarity	NPD5329	Approved
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5174	Approved
0.7879	Intermediate Similarity	NPD5175	Approved
0.7879	Intermediate Similarity	NPD4754	Approved
0.78	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD4197	Approved
0.7767	Intermediate Similarity	NPD4634	Approved
0.7766	Intermediate Similarity	NPD7515	Phase 2
0.7745	Intermediate Similarity	NPD7320	Approved
0.7745	Intermediate Similarity	NPD6881	Approved
0.7745	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD7525	Registered
0.7723	Intermediate Similarity	NPD4768	Approved
0.7723	Intermediate Similarity	NPD4767	Approved
0.7701	Intermediate Similarity	NPD3617	Approved
0.767	Intermediate Similarity	NPD6373	Approved
0.767	Intermediate Similarity	NPD6372	Approved
0.7667	Intermediate Similarity	NPD4788	Approved
0.7647	Intermediate Similarity	NPD5697	Approved
0.7647	Intermediate Similarity	NPD5701	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4138	Approved
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD4689	Approved
0.7609	Intermediate Similarity	NPD4688	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD4693	Phase 3
0.7609	Intermediate Similarity	NPD4690	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD5205	Approved
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7596	Intermediate Similarity	NPD7290	Approved
0.7596	Intermediate Similarity	NPD7102	Approved
0.7596	Intermediate Similarity	NPD6883	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7573	Intermediate Similarity	NPD5168	Approved
0.7573	Intermediate Similarity	NPD4729	Approved
0.7573	Intermediate Similarity	NPD5128	Approved
0.7573	Intermediate Similarity	NPD4730	Approved
0.7558	Intermediate Similarity	NPD3703	Phase 2
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD5210	Approved
0.7526	Intermediate Similarity	NPD4629	Approved
0.7524	Intermediate Similarity	NPD8130	Phase 1
0.7524	Intermediate Similarity	NPD6617	Approved
0.7524	Intermediate Similarity	NPD6650	Approved
0.7524	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6869	Approved
0.7524	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7453	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD6882	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7444	Intermediate Similarity	NPD4692	Approved
0.7444	Intermediate Similarity	NPD4139	Approved
0.7442	Intermediate Similarity	NPD6926	Approved
0.7442	Intermediate Similarity	NPD6924	Approved
0.7429	Intermediate Similarity	NPD5250	Approved
0.7429	Intermediate Similarity	NPD5169	Approved
0.7429	Intermediate Similarity	NPD5248	Approved
0.7429	Intermediate Similarity	NPD5247	Approved
0.7429	Intermediate Similarity	NPD5249	Phase 3
0.7429	Intermediate Similarity	NPD5135	Approved
0.7429	Intermediate Similarity	NPD5251	Approved
0.7429	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD5690	Phase 2
0.7419	Intermediate Similarity	NPD5280	Approved
0.7419	Intermediate Similarity	NPD4694	Approved
0.7396	Intermediate Similarity	NPD6411	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5127	Approved
0.7358	Intermediate Similarity	NPD5217	Approved
0.7358	Intermediate Similarity	NPD5216	Approved
0.7358	Intermediate Similarity	NPD5215	Approved
0.7339	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD4695	Discontinued
0.7317	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6054	Approved
0.7297	Intermediate Similarity	NPD6059	Approved
0.7294	Intermediate Similarity	NPD4747	Approved
0.7294	Intermediate Similarity	NPD4789	Approved
0.7294	Intermediate Similarity	NPD4245	Approved
0.7294	Intermediate Similarity	NPD4244	Approved
0.7273	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD6933	Approved
0.7248	Intermediate Similarity	NPD6868	Approved
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4785	Approved
0.7241	Intermediate Similarity	NPD4784	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7222	Intermediate Similarity	NPD4632	Approved
0.7222	Intermediate Similarity	NPD4195	Approved
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD6008	Approved
0.7209	Intermediate Similarity	NPD4243	Approved
0.7209	Intermediate Similarity	NPD7152	Approved
0.7209	Intermediate Similarity	NPD7150	Approved
0.7209	Intermediate Similarity	NPD7151	Approved
0.72	Intermediate Similarity	NPD7902	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7188	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6101	Approved
0.7176	Intermediate Similarity	NPD3698	Phase 2
0.7176	Intermediate Similarity	NPD6922	Approved
0.7176	Intermediate Similarity	NPD4137	Phase 3
0.7176	Intermediate Similarity	NPD6923	Approved
0.7172	Intermediate Similarity	NPD5695	Phase 3
0.7168	Intermediate Similarity	NPD6370	Approved
0.7158	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD4748	Discontinued
0.7129	Intermediate Similarity	NPD7638	Approved
0.7129	Intermediate Similarity	NPD5696	Approved
0.7117	Intermediate Similarity	NPD6335	Approved
0.7111	Intermediate Similarity	NPD6114	Approved
0.7111	Intermediate Similarity	NPD6697	Approved
0.7111	Intermediate Similarity	NPD6118	Approved
0.7111	Intermediate Similarity	NPD6115	Approved
0.7093	Intermediate Similarity	NPD7144	Approved
0.7093	Intermediate Similarity	NPD7143	Approved
0.7093	Intermediate Similarity	NPD4691	Approved
0.7091	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD6015	Approved
0.7059	Intermediate Similarity	NPD5360	Phase 3
0.7059	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7639	Approved
0.7054	Intermediate Similarity	NPD7100	Approved
0.7054	Intermediate Similarity	NPD7101	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7045	Intermediate Similarity	NPD5733	Approved
0.7043	Intermediate Similarity	NPD7492	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.7033	Intermediate Similarity	NPD6929	Approved
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7018	Intermediate Similarity	NPD5988	Approved
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.701	Intermediate Similarity	NPD7285	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data