NPASS Compound

Structure

NPC41554 OpenBabel07101719132D 33 36 0 0 1 0 0 0 0 0999 V2000 -7.9111 -2.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9580 -4.9884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5607 -4.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1028 -4.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 -3.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9594 -2.6169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7056 -3.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3566 -3.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0251 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -1.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6090 -4.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 -3.6584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3083 -3.3400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4532 -2.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 -2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 1 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 2.5279 0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 27 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 24 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 20 7 1 1 0 0 0 21 30 1 1 0 0 0 22 26 1 1 0 0 0 23 24 1 0 0 0 0 23 26 1 1 0 0 0 24 28 1 0 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 32 1 6 0 0 0 29 27 1 6 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.36
Volume:	505.802
LogP:	4.547
LogD:	4.562
LogS:	-4.385
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	5.208
Fsp3:	0.862
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:	-4.914
MDCK Permeability:	5.602312376140617e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.808

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	85.45178985595703%
Volume Distribution (VD):	1.082
Pgp-substrate:	2.079606771469116%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.323
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	1.328
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.076
Carcinogencity:	0.003
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC41554

Natural Product ID:	NPC41554
*Common Name:**	(3S,5R,6R,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5-Ethyl-6-Methylhept-3-En-2-Yl]-10,13-Dimethyl-2,3,4,6,11,12,14,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthrene-3,5,6,9-Tetrol
IUPAC Name:	(3S,5R,6R,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,6,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,5,6,9-tetrol
Synonyms:
Standard InCHIKey:	NDOKWZQNNLRVLS-RRAGNSSVSA-N
Standard InCHI:	InChI=1S/C29H48O4/c1-7-20(18(2)3)9-8-19(4)22-10-11-23-24-16-25(31)29(33)17-21(30)12-13-27(29,6)28(24,32)15-14-26(22,23)5/h8-9,16,18-23,25,30-33H,7,10-15,17H2,1-6H3/b9-8+/t19-,20+,21+,22-,23+,25-,26-,27-,28-,29+/m1/s1
SMILES:	CC[C@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C2=C[C@H]([C@@]2([C@]1(C)CC[C@@H](C2)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492814
PubChem CID:	44566229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441084]
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9834174]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[480157]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[480157]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[480157]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[480157]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[480157]

☑ 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 NPC41554 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	177
0.1-0.2	1360
0.2-0.3	4683
0.3-0.4	12022
0.4-0.5	11179
0.5-0.6	5983
0.6-0.7	5212
0.7-0.8	1712
0.8-0.85	252
0.85-0.9	88
0.9-0.95	18
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97404
0.9882	High Similarity	NPC291484
0.9882	High Similarity	NPC329596
0.9882	High Similarity	NPC11216
0.9882	High Similarity	NPC80561
0.9882	High Similarity	NPC204188
0.9882	High Similarity	NPC3345
0.9765	High Similarity	NPC470361
0.9551	High Similarity	NPC288970
0.9432	High Similarity	NPC310013
0.9419	High Similarity	NPC133588
0.9419	High Similarity	NPC474668
0.9412	High Similarity	NPC261266
0.9412	High Similarity	NPC299068
0.9412	High Similarity	NPC6391
0.9326	High Similarity	NPC65402
0.9326	High Similarity	NPC127718
0.9294	High Similarity	NPC470360
0.9222	High Similarity	NPC8774
0.9176	High Similarity	NPC205845
0.9176	High Similarity	NPC185568
0.9121	High Similarity	NPC98457
0.9121	High Similarity	NPC227583
0.9121	High Similarity	NPC12103
0.9101	High Similarity	NPC275671
0.9059	High Similarity	NPC474634
0.9022	High Similarity	NPC261807
0.8989	High Similarity	NPC270511
0.8989	High Similarity	NPC295668
0.8989	High Similarity	NPC470390
0.8989	High Similarity	NPC14380
0.8989	High Similarity	NPC192437
0.8989	High Similarity	NPC475751
0.8989	High Similarity	NPC473956
0.8989	High Similarity	NPC245410
0.8977	High Similarity	NPC67872
0.8966	High Similarity	NPC152808
0.8966	High Similarity	NPC293287
0.8941	High Similarity	NPC30166
0.8941	High Similarity	NPC101462
0.8941	High Similarity	NPC50964
0.8941	High Similarity	NPC49964
0.8913	High Similarity	NPC103165
0.8913	High Similarity	NPC210717
0.8901	High Similarity	NPC477605
0.8876	High Similarity	NPC109744
0.8876	High Similarity	NPC101886
0.8864	High Similarity	NPC470620
0.8864	High Similarity	NPC149224
0.8837	High Similarity	NPC317458
0.8824	High Similarity	NPC209620
0.8824	High Similarity	NPC470383
0.8824	High Similarity	NPC23852
0.8824	High Similarity	NPC249423
0.8824	High Similarity	NPC476646
0.8824	High Similarity	NPC264245
0.8817	High Similarity	NPC477226
0.8817	High Similarity	NPC476893
0.8764	High Similarity	NPC280556
0.8764	High Similarity	NPC212596
0.8764	High Similarity	NPC4574
0.8764	High Similarity	NPC475664
0.8764	High Similarity	NPC475605
0.875	High Similarity	NPC201273
0.875	High Similarity	NPC94462
0.875	High Similarity	NPC6605
0.875	High Similarity	NPC139724
0.8736	High Similarity	NPC124172
0.8723	High Similarity	NPC476895
0.8721	High Similarity	NPC296701
0.8721	High Similarity	NPC87489
0.8721	High Similarity	NPC218616
0.871	High Similarity	NPC72204
0.8706	High Similarity	NPC241290
0.8706	High Similarity	NPC209944
0.8706	High Similarity	NPC234193
0.8706	High Similarity	NPC164840
0.8706	High Similarity	NPC96362
0.8696	High Similarity	NPC144202
0.8681	High Similarity	NPC210268
0.8667	High Similarity	NPC187785
0.8667	High Similarity	NPC105495
0.8667	High Similarity	NPC259875
0.8667	High Similarity	NPC138974
0.8652	High Similarity	NPC474657
0.8652	High Similarity	NPC186145
0.8652	High Similarity	NPC304083
0.8636	High Similarity	NPC274448
0.8636	High Similarity	NPC318390
0.8636	High Similarity	NPC266511
0.8621	High Similarity	NPC211135
0.8621	High Similarity	NPC85095
0.8621	High Similarity	NPC216420
0.8621	High Similarity	NPC320548
0.8621	High Similarity	NPC207013
0.8605	High Similarity	NPC474531
0.8605	High Similarity	NPC47761
0.8602	High Similarity	NPC476894
0.8588	High Similarity	NPC47982
0.8588	High Similarity	NPC109546
0.8588	High Similarity	NPC209430
0.8588	High Similarity	NPC328714
0.8588	High Similarity	NPC81306
0.8588	High Similarity	NPC84694
0.8588	High Similarity	NPC143182
0.8588	High Similarity	NPC30986
0.8588	High Similarity	NPC28862
0.8587	High Similarity	NPC137461
0.8587	High Similarity	NPC27531
0.8586	High Similarity	NPC472219
0.8586	High Similarity	NPC472218
0.8586	High Similarity	NPC472217
0.8542	High Similarity	NPC476896
0.8539	High Similarity	NPC71520
0.8539	High Similarity	NPC24277
0.8539	High Similarity	NPC121981
0.8539	High Similarity	NPC269058
0.8523	High Similarity	NPC475798
0.8523	High Similarity	NPC238485
0.8523	High Similarity	NPC470077
0.8523	High Similarity	NPC127606
0.8523	High Similarity	NPC231310
0.8511	High Similarity	NPC471903
0.8506	High Similarity	NPC7988
0.8506	High Similarity	NPC470614
0.8506	High Similarity	NPC1272
0.8488	Intermediate Similarity	NPC102253
0.8488	Intermediate Similarity	NPC13554
0.8488	Intermediate Similarity	NPC287749
0.8488	Intermediate Similarity	NPC322313
0.8488	Intermediate Similarity	NPC236237
0.8488	Intermediate Similarity	NPC236112
0.8478	Intermediate Similarity	NPC114389
0.8471	Intermediate Similarity	NPC167891
0.8471	Intermediate Similarity	NPC87604
0.8471	Intermediate Similarity	NPC474216
0.8471	Intermediate Similarity	NPC83351
0.8462	Intermediate Similarity	NPC477606
0.8444	Intermediate Similarity	NPC475313
0.8427	Intermediate Similarity	NPC157257
0.8409	Intermediate Similarity	NPC82623
0.8409	Intermediate Similarity	NPC477818
0.8409	Intermediate Similarity	NPC113978
0.8409	Intermediate Similarity	NPC141941
0.8409	Intermediate Similarity	NPC475789
0.8409	Intermediate Similarity	NPC232023
0.8409	Intermediate Similarity	NPC110778
0.8409	Intermediate Similarity	NPC470384
0.8409	Intermediate Similarity	NPC193870
0.8391	Intermediate Similarity	NPC471270
0.8391	Intermediate Similarity	NPC320525
0.8387	Intermediate Similarity	NPC119379
0.8387	Intermediate Similarity	NPC98193
0.8384	Intermediate Similarity	NPC166607
0.8372	Intermediate Similarity	NPC80530
0.8372	Intermediate Similarity	NPC273410
0.8367	Intermediate Similarity	NPC247957
0.8367	Intermediate Similarity	NPC249187
0.8353	Intermediate Similarity	NPC318495
0.8353	Intermediate Similarity	NPC91594
0.8353	Intermediate Similarity	NPC155986
0.8353	Intermediate Similarity	NPC477924
0.8353	Intermediate Similarity	NPC198968
0.8353	Intermediate Similarity	NPC130136
0.8353	Intermediate Similarity	NPC471798
0.8352	Intermediate Similarity	NPC470542
0.8351	Intermediate Similarity	NPC475617
0.8333	Intermediate Similarity	NPC237344
0.8333	Intermediate Similarity	NPC125399
0.8317	Intermediate Similarity	NPC472216
0.8317	Intermediate Similarity	NPC284828
0.8317	Intermediate Similarity	NPC5475
0.8317	Intermediate Similarity	NPC173905
0.8315	Intermediate Similarity	NPC474047
0.8315	Intermediate Similarity	NPC474493
0.8315	Intermediate Similarity	NPC83702
0.8315	Intermediate Similarity	NPC256567
0.8315	Intermediate Similarity	NPC255882
0.8315	Intermediate Similarity	NPC209802
0.8315	Intermediate Similarity	NPC15534
0.8298	Intermediate Similarity	NPC279410
0.8298	Intermediate Similarity	NPC119562
0.8295	Intermediate Similarity	NPC470049
0.8295	Intermediate Similarity	NPC189972
0.8295	Intermediate Similarity	NPC248886
0.8295	Intermediate Similarity	NPC202389
0.8283	Intermediate Similarity	NPC160843
0.8283	Intermediate Similarity	NPC473543
0.8283	Intermediate Similarity	NPC75608
0.8276	Intermediate Similarity	NPC471266
0.8276	Intermediate Similarity	NPC95124
0.8276	Intermediate Similarity	NPC22403
0.8276	Intermediate Similarity	NPC236707
0.8276	Intermediate Similarity	NPC324772
0.8276	Intermediate Similarity	NPC26117
0.8265	Intermediate Similarity	NPC300399
0.8265	Intermediate Similarity	NPC471482
0.8261	Intermediate Similarity	NPC115607
0.8256	Intermediate Similarity	NPC244385
0.8256	Intermediate Similarity	NPC473943

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 NPC41554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1532
0.2-0.3	4092
0.3-0.4	2263
0.4-0.5	639
0.5-0.6	189
0.6-0.7	177
0.7-0.8	77
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD7525	Registered
0.8315	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7514	Phase 3
0.8276	Intermediate Similarity	NPD6930	Phase 2
0.8276	Intermediate Similarity	NPD6931	Approved
0.8242	Intermediate Similarity	NPD7524	Approved
0.8242	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6695	Phase 3
0.8161	Intermediate Similarity	NPD6929	Approved
0.8118	Intermediate Similarity	NPD6942	Approved
0.8118	Intermediate Similarity	NPD7339	Approved
0.8068	Intermediate Similarity	NPD7332	Phase 2
0.8046	Intermediate Similarity	NPD7145	Approved
0.7978	Intermediate Similarity	NPD6902	Approved
0.7931	Intermediate Similarity	NPD5776	Phase 2
0.7931	Intermediate Similarity	NPD6925	Approved
0.7931	Intermediate Similarity	NPD6932	Approved
0.7849	Intermediate Similarity	NPD7750	Discontinued
0.7826	Intermediate Similarity	NPD6893	Approved
0.7816	Intermediate Similarity	NPD6933	Approved
0.7816	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4785	Approved
0.7586	Intermediate Similarity	NPD4784	Approved
0.7586	Intermediate Similarity	NPD6926	Approved
0.7586	Intermediate Similarity	NPD6924	Approved
0.7582	Intermediate Similarity	NPD6898	Phase 1
0.7556	Intermediate Similarity	NPD7645	Phase 2
0.7556	Intermediate Similarity	NPD6683	Phase 2
0.7549	Intermediate Similarity	NPD5211	Phase 2
0.7527	Intermediate Similarity	NPD4786	Approved
0.7526	Intermediate Similarity	NPD7087	Discontinued
0.7444	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5141	Approved
0.7383	Intermediate Similarity	NPD4634	Approved
0.7356	Intermediate Similarity	NPD7151	Approved
0.7356	Intermediate Similarity	NPD7152	Approved
0.7356	Intermediate Similarity	NPD7150	Approved
0.7356	Intermediate Similarity	NPD4243	Approved
0.7353	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD5285	Approved
0.7353	Intermediate Similarity	NPD4696	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD6079	Approved
0.7347	Intermediate Similarity	NPD7637	Suspended
0.7327	Intermediate Similarity	NPD4755	Approved
0.7326	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5328	Approved
0.7312	Intermediate Similarity	NPD3667	Approved
0.7303	Intermediate Similarity	NPD8264	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7283	Intermediate Similarity	NPD4748	Discontinued
0.7283	Intermediate Similarity	NPD7509	Discontinued
0.7273	Intermediate Similarity	NPD4202	Approved
0.7255	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD7144	Approved
0.7241	Intermediate Similarity	NPD7143	Approved
0.7232	Intermediate Similarity	NPD7327	Approved
0.7232	Intermediate Similarity	NPD7328	Approved
0.7212	Intermediate Similarity	NPD5224	Approved
0.7212	Intermediate Similarity	NPD5225	Approved
0.7212	Intermediate Similarity	NPD4633	Approved
0.7212	Intermediate Similarity	NPD5226	Approved
0.7188	Intermediate Similarity	NPD3618	Phase 1
0.7184	Intermediate Similarity	NPD4700	Approved
0.7168	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7126	Intermediate Similarity	NPD6923	Approved
0.7126	Intermediate Similarity	NPD6922	Approved
0.7115	Intermediate Similarity	NPD4159	Approved
0.7115	Intermediate Similarity	NPD5223	Approved
0.71	Intermediate Similarity	NPD6399	Phase 3
0.7071	Intermediate Similarity	NPD7136	Phase 2
0.7059	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD5221	Approved
0.7043	Intermediate Similarity	NPD8296	Approved
0.7043	Intermediate Similarity	NPD8033	Approved
0.7043	Intermediate Similarity	NPD8380	Approved
0.7043	Intermediate Similarity	NPD8335	Approved
0.7043	Intermediate Similarity	NPD7503	Approved
0.7043	Intermediate Similarity	NPD8378	Approved
0.7043	Intermediate Similarity	NPD8379	Approved
0.7037	Intermediate Similarity	NPD6899	Approved
0.7037	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD5173	Approved
0.6989	Remote Similarity	NPD4195	Approved
0.697	Remote Similarity	NPD4753	Phase 2
0.6957	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD8377	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6944	Remote Similarity	NPD5697	Approved
0.6937	Remote Similarity	NPD8297	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD4190	Phase 3
0.6923	Remote Similarity	NPD5275	Approved
0.6909	Remote Similarity	NPD7290	Approved
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.6893	Remote Similarity	NPD4697	Phase 3
0.6881	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD7320	Approved
0.6881	Remote Similarity	NPD4730	Approved
0.6852	Remote Similarity	NPD4768	Approved
0.6852	Remote Similarity	NPD4767	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD6617	Approved
0.6847	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD4754	Approved
0.6818	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6013	Approved
0.6818	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6818	Remote Similarity	NPD6012	Approved
0.6818	Remote Similarity	NPD6373	Approved
0.681	Remote Similarity	NPD6319	Approved
0.681	Remote Similarity	NPD6054	Approved
0.6804	Remote Similarity	NPD3668	Phase 3
0.6804	Remote Similarity	NPD3666	Approved
0.6804	Remote Similarity	NPD3665	Phase 1
0.6804	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD6051	Approved
0.6796	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD4629	Approved
0.6789	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD5701	Approved
0.6786	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD5249	Phase 3
0.6757	Remote Similarity	NPD5250	Approved
0.6757	Remote Similarity	NPD5251	Approved
0.6757	Remote Similarity	NPD5247	Approved
0.6757	Remote Similarity	NPD5248	Approved
0.6735	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD6011	Approved
0.6727	Remote Similarity	NPD5128	Approved
0.6706	Remote Similarity	NPD368	Approved
0.6697	Remote Similarity	NPD6640	Phase 3
0.6696	Remote Similarity	NPD5217	Approved
0.6696	Remote Similarity	NPD5215	Approved
0.6696	Remote Similarity	NPD5216	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD7319	Approved
0.661	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD6015	Approved
0.6607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD5135	Approved
0.6604	Remote Similarity	NPD5290	Discontinued
0.6598	Remote Similarity	NPD4223	Phase 3
0.6598	Remote Similarity	NPD4221	Approved
0.6583	Remote Similarity	NPD7492	Approved
0.6566	Remote Similarity	NPD5329	Approved
0.6562	Remote Similarity	NPD4821	Approved
0.6562	Remote Similarity	NPD4822	Approved
0.6562	Remote Similarity	NPD4819	Approved
0.6562	Remote Similarity	NPD4820	Approved
0.6555	Remote Similarity	NPD5988	Approved
0.6549	Remote Similarity	NPD5127	Approved
0.6549	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD6648	Approved
0.6529	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD7741	Discontinued
0.6522	Remote Similarity	NPD4732	Discontinued
0.6505	Remote Similarity	NPD8034	Phase 2
0.6505	Remote Similarity	NPD8035	Phase 2
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4519	Discontinued
0.65	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD4623	Approved
0.6475	Remote Similarity	NPD7078	Approved
0.6471	Remote Similarity	NPD5983	Phase 2
0.6465	Remote Similarity	NPD4197	Approved
0.646	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD4522	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6429	Remote Similarity	NPD5168	Approved
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6686	Approved
0.6423	Remote Similarity	NPD7736	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