NPASS Compound

Structure

CID161147 OpenBabel06191715532D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.0614 5.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5586 5.0579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2911 3.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9059 3.1317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6414 1.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8203 0.5083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7882 3.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4031 2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8200 -1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2808 0.9458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2805 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4602 -0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6403 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6408 -1.8941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8208 1.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6174 4.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2322 4.0948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4619 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8208 -1.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4605 -1.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4616 1.4197 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6408 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8203 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6411 0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8205 -0.4734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3019 -1.9057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 1.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6823 0.9719 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 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 27 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 6 0 0 0 23 24 2 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.3
Volume:	471.807
LogP:	5.254
LogD:	4.171
LogS:	-5.398
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	5.199
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.987
MDCK Permeability:	2.4657047106302343e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.205
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	89.00443267822266%
Volume Distribution (VD):	1.222
Pgp-substrate:	1.7886046171188354%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.518
CYP2C19-inhibitor:	0.237
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.936

ADMET: Excretion

Clearance (CL):	1.149
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.38
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.483
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.581
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC161147

Natural Product ID:	NPC161147
*Common Name:**	9Alpha,11Alpha-Dihydroxyergosta-4,6,8(14),22-Tetraen-3-One
IUPAC Name:	(9S,10S,11R,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-9,11-dihydroxy-10,13-dimethyl-2,11,12,15,16,17-hexahydro-1H-cyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	GBAGTCNHJJTJIL-YVVZYAQMSA-N
Standard InCHI:	InChI=1S/C28H40O3/c1-17(2)18(3)7-8-19(4)22-11-12-23-24-10-9-20-15-21(29)13-14-27(20,6)28(24,31)25(30)16-26(22,23)5/h7-10,15,17-19,22,25,30-31H,11-14,16H2,1-6H3/b8-7+/t18-,19+,22+,25+,26+,27-,28-/m0/s1
SMILES:	CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CCC2=C3C=CC4=CC(=O)CC[C@]4(C)[C@]3([C@@H](C[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784265
PubChem CID:	53355590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30158	Sorangiineae	Genus	n.a.	Bacteria	n.a.	latex	n.a.	PMID[21513291]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	10000.0	nM	PMID[551614]

☑ 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 NPC161147 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	186
0.1-0.2	935
0.2-0.3	4178
0.3-0.4	11138
0.4-0.5	13278
0.5-0.6	7946
0.6-0.7	4198
0.7-0.8	788
0.8-0.85	43
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC287079
0.8936	High Similarity	NPC259286
0.8842	High Similarity	NPC249954
0.8776	High Similarity	NPC473424
0.875	High Similarity	NPC474785
0.875	High Similarity	NPC474938
0.8723	High Similarity	NPC69454
0.8632	High Similarity	NPC472977
0.8632	High Similarity	NPC472976
0.8617	High Similarity	NPC63748
0.8454	Intermediate Similarity	NPC471463
0.8438	Intermediate Similarity	NPC299100
0.8438	Intermediate Similarity	NPC474690
0.8438	Intermediate Similarity	NPC473162
0.8421	Intermediate Similarity	NPC475806
0.8404	Intermediate Similarity	NPC472973
0.8404	Intermediate Similarity	NPC275740
0.8404	Intermediate Similarity	NPC86319
0.84	Intermediate Similarity	NPC477915
0.8351	Intermediate Similarity	NPC473170
0.8351	Intermediate Similarity	NPC180950
0.8333	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC109305
0.8333	Intermediate Similarity	NPC323834
0.8333	Intermediate Similarity	NPC149047
0.8333	Intermediate Similarity	NPC472930
0.8317	Intermediate Similarity	NPC475050
0.8316	Intermediate Similarity	NPC48010
0.8298	Intermediate Similarity	NPC471722
0.8298	Intermediate Similarity	NPC143767
0.8298	Intermediate Similarity	NPC131470
0.8283	Intermediate Similarity	NPC103051
0.8283	Intermediate Similarity	NPC471717
0.828	Intermediate Similarity	NPC472974
0.8269	Intermediate Similarity	NPC214644
0.8265	Intermediate Similarity	NPC117133
0.8252	Intermediate Similarity	NPC220229
0.8252	Intermediate Similarity	NPC475060
0.8247	Intermediate Similarity	NPC8993
0.8247	Intermediate Similarity	NPC473172
0.8235	Intermediate Similarity	NPC204833
0.8235	Intermediate Similarity	NPC209502
0.8229	Intermediate Similarity	NPC233116
0.8229	Intermediate Similarity	NPC19114
0.8229	Intermediate Similarity	NPC472978
0.8211	Intermediate Similarity	NPC309603
0.8211	Intermediate Similarity	NPC123912
0.8211	Intermediate Similarity	NPC473999
0.82	Intermediate Similarity	NPC316964
0.8191	Intermediate Similarity	NPC141292
0.8173	Intermediate Similarity	NPC217201
0.8173	Intermediate Similarity	NPC65941
0.8172	Intermediate Similarity	NPC470574
0.8163	Intermediate Similarity	NPC174948
0.8163	Intermediate Similarity	NPC472932
0.8163	Intermediate Similarity	NPC173875
0.8163	Intermediate Similarity	NPC200702
0.8163	Intermediate Similarity	NPC318282
0.8163	Intermediate Similarity	NPC469995
0.8163	Intermediate Similarity	NPC271195
0.8155	Intermediate Similarity	NPC260268
0.8155	Intermediate Similarity	NPC214264
0.8155	Intermediate Similarity	NPC150531
0.8155	Intermediate Similarity	NPC296945
0.8155	Intermediate Similarity	NPC48733
0.8155	Intermediate Similarity	NPC50692
0.8155	Intermediate Similarity	NPC476027
0.8155	Intermediate Similarity	NPC171137
0.8155	Intermediate Similarity	NPC152695
0.8155	Intermediate Similarity	NPC202167
0.8155	Intermediate Similarity	NPC97202
0.8155	Intermediate Similarity	NPC85829
0.8155	Intermediate Similarity	NPC319077
0.8155	Intermediate Similarity	NPC302607
0.8155	Intermediate Similarity	NPC49958
0.8152	Intermediate Similarity	NPC110150
0.8152	Intermediate Similarity	NPC66764
0.8144	Intermediate Similarity	NPC134826
0.8132	Intermediate Similarity	NPC470298
0.8125	Intermediate Similarity	NPC69622
0.8125	Intermediate Similarity	NPC183283
0.8119	Intermediate Similarity	NPC163372
0.8119	Intermediate Similarity	NPC302537
0.8105	Intermediate Similarity	NPC328539
0.8105	Intermediate Similarity	NPC310752
0.8105	Intermediate Similarity	NPC292491
0.8105	Intermediate Similarity	NPC158778
0.8095	Intermediate Similarity	NPC11710
0.8085	Intermediate Similarity	NPC118648
0.8085	Intermediate Similarity	NPC72133
0.8085	Intermediate Similarity	NPC475022
0.8085	Intermediate Similarity	NPC89077
0.8085	Intermediate Similarity	NPC183736
0.8085	Intermediate Similarity	NPC222613
0.8081	Intermediate Similarity	NPC301534
0.8081	Intermediate Similarity	NPC250757
0.8081	Intermediate Similarity	NPC473164
0.8081	Intermediate Similarity	NPC328371
0.8077	Intermediate Similarity	NPC473284
0.8077	Intermediate Similarity	NPC477916
0.8077	Intermediate Similarity	NPC83744
0.8061	Intermediate Similarity	NPC469406
0.8061	Intermediate Similarity	NPC166906
0.8061	Intermediate Similarity	NPC196227
0.8041	Intermediate Similarity	NPC155304
0.8041	Intermediate Similarity	NPC472975
0.8041	Intermediate Similarity	NPC473998
0.8041	Intermediate Similarity	NPC116726
0.8039	Intermediate Similarity	NPC119601
0.8039	Intermediate Similarity	NPC308726
0.8021	Intermediate Similarity	NPC32830
0.802	Intermediate Similarity	NPC266955
0.8	Intermediate Similarity	NPC58063
0.8	Intermediate Similarity	NPC329417
0.8	Intermediate Similarity	NPC475740
0.8	Intermediate Similarity	NPC136548
0.8	Intermediate Similarity	NPC320306
0.798	Intermediate Similarity	NPC317586
0.798	Intermediate Similarity	NPC127063
0.798	Intermediate Similarity	NPC470016
0.7979	Intermediate Similarity	NPC474083
0.7961	Intermediate Similarity	NPC311612
0.7961	Intermediate Similarity	NPC249187
0.7961	Intermediate Similarity	NPC473624
0.7961	Intermediate Similarity	NPC247957
0.7961	Intermediate Similarity	NPC111323
0.7959	Intermediate Similarity	NPC472942
0.7957	Intermediate Similarity	NPC476082
0.7957	Intermediate Similarity	NPC169941
0.7957	Intermediate Similarity	NPC278648
0.7957	Intermediate Similarity	NPC251475
0.7941	Intermediate Similarity	NPC115899
0.7941	Intermediate Similarity	NPC282524
0.7938	Intermediate Similarity	NPC191684
0.7921	Intermediate Similarity	NPC166745
0.7921	Intermediate Similarity	NPC235464
0.7921	Intermediate Similarity	NPC197386
0.7917	Intermediate Similarity	NPC44181
0.7905	Intermediate Similarity	NPC472925
0.7905	Intermediate Similarity	NPC329048
0.7905	Intermediate Similarity	NPC330011
0.7905	Intermediate Similarity	NPC185
0.79	Intermediate Similarity	NPC96859
0.79	Intermediate Similarity	NPC328162
0.79	Intermediate Similarity	NPC305483
0.7895	Intermediate Similarity	NPC31564
0.7895	Intermediate Similarity	NPC472985
0.7895	Intermediate Similarity	NPC474732
0.7895	Intermediate Similarity	NPC473168
0.7895	Intermediate Similarity	NPC474733
0.7895	Intermediate Similarity	NPC145879
0.7895	Intermediate Similarity	NPC474778
0.7895	Intermediate Similarity	NPC472986
0.7879	Intermediate Similarity	NPC470957
0.7879	Intermediate Similarity	NPC470958
0.7879	Intermediate Similarity	NPC292793
0.7872	Intermediate Similarity	NPC231310
0.7872	Intermediate Similarity	NPC473246
0.7872	Intermediate Similarity	NPC476412
0.7872	Intermediate Similarity	NPC238485
0.7872	Intermediate Similarity	NPC40687
0.7864	Intermediate Similarity	NPC204450
0.7864	Intermediate Similarity	NPC195290
0.7864	Intermediate Similarity	NPC87351
0.7857	Intermediate Similarity	NPC185936
0.7857	Intermediate Similarity	NPC272746
0.7857	Intermediate Similarity	NPC212948
0.7857	Intermediate Similarity	NPC473167
0.7857	Intermediate Similarity	NPC168027
0.785	Intermediate Similarity	NPC76084
0.785	Intermediate Similarity	NPC37116
0.7843	Intermediate Similarity	NPC51370
0.7843	Intermediate Similarity	NPC154072
0.7843	Intermediate Similarity	NPC327431
0.7843	Intermediate Similarity	NPC287833
0.7843	Intermediate Similarity	NPC112167
0.7835	Intermediate Similarity	NPC84271
0.7835	Intermediate Similarity	NPC250592
0.7835	Intermediate Similarity	NPC31985
0.7835	Intermediate Similarity	NPC186688
0.7835	Intermediate Similarity	NPC77168
0.7835	Intermediate Similarity	NPC77263
0.7835	Intermediate Similarity	NPC229871
0.7835	Intermediate Similarity	NPC102414
0.7835	Intermediate Similarity	NPC473100
0.7835	Intermediate Similarity	NPC2983
0.7835	Intermediate Similarity	NPC214387
0.7835	Intermediate Similarity	NPC1015
0.7835	Intermediate Similarity	NPC469319
0.783	Intermediate Similarity	NPC295244
0.7822	Intermediate Similarity	NPC470522
0.7822	Intermediate Similarity	NPC253826
0.7822	Intermediate Similarity	NPC135685
0.7812	Intermediate Similarity	NPC138756
0.7812	Intermediate Similarity	NPC472324
0.781	Intermediate Similarity	NPC478052
0.781	Intermediate Similarity	NPC257353
0.781	Intermediate Similarity	NPC166607
0.7798	Intermediate Similarity	NPC108721
0.7798	Intermediate Similarity	NPC73300

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 NPC161147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1310
0.2-0.3	3758
0.3-0.4	2694
0.4-0.5	752
0.5-0.6	225
0.6-0.7	215
0.7-0.8	35
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
0.8229	Intermediate Similarity	NPD6079	Approved
0.8211	Intermediate Similarity	NPD5328	Approved
0.7895	Intermediate Similarity	NPD5279	Phase 3
0.7895	Intermediate Similarity	NPD3618	Phase 1
0.7864	Intermediate Similarity	NPD5211	Phase 2
0.7732	Intermediate Similarity	NPD4518	Approved
0.7723	Intermediate Similarity	NPD5221	Approved
0.7723	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD5222	Approved
0.7714	Intermediate Similarity	NPD5141	Approved
0.7684	Intermediate Similarity	NPD4786	Approved
0.767	Intermediate Similarity	NPD4696	Approved
0.767	Intermediate Similarity	NPD5285	Approved
0.767	Intermediate Similarity	NPD5286	Approved
0.766	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD5173	Approved
0.7647	Intermediate Similarity	NPD4755	Approved
0.76	Intermediate Similarity	NPD4202	Approved
0.7596	Intermediate Similarity	NPD5223	Approved
0.7549	Intermediate Similarity	NPD4697	Phase 3
0.7524	Intermediate Similarity	NPD5224	Approved
0.7524	Intermediate Similarity	NPD5225	Approved
0.7524	Intermediate Similarity	NPD5226	Approved
0.7524	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.7453	Intermediate Similarity	NPD5175	Approved
0.7453	Intermediate Similarity	NPD5174	Approved
0.7447	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7426	Intermediate Similarity	NPD5778	Approved
0.7426	Intermediate Similarity	NPD5779	Approved
0.7364	Intermediate Similarity	NPD4634	Approved
0.7347	Intermediate Similarity	NPD5280	Approved
0.7347	Intermediate Similarity	NPD4694	Approved
0.7339	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7315	Intermediate Similarity	NPD6402	Approved
0.7315	Intermediate Similarity	NPD7128	Approved
0.7315	Intermediate Similarity	NPD5739	Approved
0.7315	Intermediate Similarity	NPD6675	Approved
0.73	Intermediate Similarity	NPD6101	Approved
0.73	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4754	Approved
0.7283	Intermediate Similarity	NPD8264	Approved
0.7248	Intermediate Similarity	NPD5697	Approved
0.7245	Intermediate Similarity	NPD1696	Phase 3
0.7232	Intermediate Similarity	NPD8297	Approved
0.7207	Intermediate Similarity	NPD6883	Approved
0.7207	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD7102	Approved
0.7204	Intermediate Similarity	NPD6933	Approved
0.7182	Intermediate Similarity	NPD7320	Approved
0.7182	Intermediate Similarity	NPD4729	Approved
0.7182	Intermediate Similarity	NPD4730	Approved
0.7182	Intermediate Similarity	NPD6011	Approved
0.7172	Intermediate Similarity	NPD5690	Phase 2
0.7172	Intermediate Similarity	NPD4623	Approved
0.7172	Intermediate Similarity	NPD4519	Discontinued
0.7168	Intermediate Similarity	NPD4632	Approved
0.7157	Intermediate Similarity	NPD5284	Approved
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD5281	Approved
0.7156	Intermediate Similarity	NPD4767	Approved
0.7156	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7117	Intermediate Similarity	NPD6013	Approved
0.7117	Intermediate Similarity	NPD6373	Approved
0.7117	Intermediate Similarity	NPD6012	Approved
0.7117	Intermediate Similarity	NPD6372	Approved
0.7117	Intermediate Similarity	NPD6014	Approved
0.7113	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD4223	Phase 3
0.7091	Intermediate Similarity	NPD5701	Approved
0.708	Intermediate Similarity	NPD6882	Approved
0.7071	Intermediate Similarity	NPD5329	Approved
0.7059	Intermediate Similarity	NPD4096	Approved
0.7054	Intermediate Similarity	NPD5249	Phase 3
0.7054	Intermediate Similarity	NPD5248	Approved
0.7054	Intermediate Similarity	NPD5250	Approved
0.7054	Intermediate Similarity	NPD5169	Approved
0.7054	Intermediate Similarity	NPD5251	Approved
0.7054	Intermediate Similarity	NPD5247	Approved
0.7054	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5135	Approved
0.7053	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5128	Approved
0.7027	Intermediate Similarity	NPD5168	Approved
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5127	Approved
0.6991	Remote Similarity	NPD5215	Approved
0.6991	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5216	Approved
0.6991	Remote Similarity	NPD5217	Approved
0.6989	Remote Similarity	NPD6924	Approved
0.6989	Remote Similarity	NPD6926	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.697	Remote Similarity	NPD4197	Approved
0.6952	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6916	Remote Similarity	NPD7638	Approved
0.6907	Remote Similarity	NPD7514	Phase 3
0.6907	Remote Similarity	NPD6931	Approved
0.6907	Remote Similarity	NPD6930	Phase 2
0.69	Remote Similarity	NPD5363	Approved
0.6893	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7748	Approved
0.6838	Remote Similarity	NPD6009	Approved
0.6832	Remote Similarity	NPD4693	Phase 3
0.6832	Remote Similarity	NPD4689	Approved
0.6832	Remote Similarity	NPD6684	Approved
0.6832	Remote Similarity	NPD4138	Approved
0.6832	Remote Similarity	NPD7334	Approved
0.6832	Remote Similarity	NPD4688	Approved
0.6832	Remote Similarity	NPD5786	Approved
0.6832	Remote Similarity	NPD5205	Approved
0.6832	Remote Similarity	NPD4690	Approved
0.6832	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD7521	Approved
0.6832	Remote Similarity	NPD7146	Approved
0.6832	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD6084	Phase 2
0.6822	Remote Similarity	NPD6083	Phase 2
0.681	Remote Similarity	NPD5167	Approved
0.6809	Remote Similarity	NPD5733	Approved
0.6809	Remote Similarity	NPD4687	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6804	Remote Similarity	NPD6929	Approved
0.6792	Remote Similarity	NPD5695	Phase 3
0.678	Remote Similarity	NPD6335	Approved
0.6778	Remote Similarity	NPD7331	Phase 2
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6774	Remote Similarity	NPD5276	Approved
0.6768	Remote Similarity	NPD4270	Approved
0.6768	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD7524	Approved
0.6762	Remote Similarity	NPD5133	Approved
0.6759	Remote Similarity	NPD4225	Approved
0.6752	Remote Similarity	NPD6868	Approved
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD7332	Phase 2
0.6735	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5207	Approved
0.6723	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD7101	Approved
0.6701	Remote Similarity	NPD3617	Approved
0.6701	Remote Similarity	NPD7145	Approved
0.67	Remote Similarity	NPD5362	Discontinued
0.67	Remote Similarity	NPD6695	Phase 3
0.67	Remote Similarity	NPD4788	Approved
0.6699	Remote Similarity	NPD6903	Approved
0.6699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6404	Discontinued
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD6317	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6313	Approved
0.6637	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4195	Approved
0.6632	Remote Similarity	NPD4058	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6612	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD6274	Approved
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6925	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