NPASS Compound

Natural Product: NPC327764

Natural Product ID	NPC327764
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LRZMCWPHMHOWNG-RDVZGMIZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5316371
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 111116 0 0 0 0 0 0 0 0999 V2000 6.5414 1.5504 -3.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3345 1.0819 -1.8571 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0140 2.2348 -0.9939 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8543 2.0946 0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8681 1.2103 1.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0017 -0.2470 0.9269 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9420 -0.7893 0.2984 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9916 -1.1006 1.5455 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1462 -2.4963 1.3712 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0873 -2.9578 2.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9041 -2.4545 3.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7260 -2.8288 4.7822 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7548 -3.7231 4.5782 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9394 -4.2287 3.3131 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1038 -3.8460 2.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9351 -3.3321 1.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7636 -2.9317 0.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1877 -3.7153 -0.0460 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -1.6668 0.8109 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1745 -1.1787 0.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0634 -0.8629 0.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6694 0.5341 0.9239 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9635 0.6365 0.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4092 1.6691 -0.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3863 1.4968 -2.2014 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2143 2.4546 -2.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6659 2.3744 -2.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6031 2.9180 -1.1760 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7246 2.2509 -0.2078 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9084 1.4046 -0.0541 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6918 2.5437 -0.3919 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6128 3.1131 0.9379 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9389 4.3068 0.9424 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3672 4.7511 -0.0537 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8807 5.1257 2.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7625 3.7567 -2.9482 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0105 1.7435 -2.7529 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8392 2.3533 -3.7762 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7187 1.2957 -2.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2510 1.1823 -2.8955 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2778 0.9243 -0.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4282 -0.2201 -0.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2206 -0.3477 -2.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5356 1.4716 0.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7190 2.9103 0.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6265 1.1408 1.4951 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7753 0.1187 -2.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2463 -0.6552 -0.3545 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1477 -1.5578 0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7953 -1.2392 1.1852 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4367 -2.8515 -0.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7636 -3.3281 -1.4954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0293 -4.5811 -2.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0105 -5.3781 -1.5139 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6974 -4.9117 -0.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4269 -3.6800 0.1285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8413 0.8675 2.2661 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2952 -4.6728 1.2663 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5067 2.6382 -3.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5590 1.2070 -3.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7507 1.1416 -3.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2460 0.5195 -1.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4753 0.3664 -1.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1428 2.7778 -1.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8693 2.9776 -1.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8970 1.8820 0.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6255 3.1684 0.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6465 1.4841 2.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8563 1.5007 0.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2498 -0.5904 2.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7507 -2.6862 0.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0927 -1.7460 3.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5889 -2.4378 5.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4137 -4.0251 5.4066 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7432 -4.9368 3.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2374 -4.2341 1.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5835 -3.3472 2.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1530 -2.1103 -0.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8851 -1.5549 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8050 -1.2024 1.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7328 0.6202 1.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8082 2.6376 -0.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1846 2.1187 -4.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2227 3.0915 -3.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0711 1.3693 -2.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4809 4.0374 -1.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1710 0.6269 -0.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1616 1.1528 1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6122 4.7431 2.9338 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8495 5.0953 2.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0895 6.1988 2.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1852 4.3407 -3.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8051 -1.2970 -1.8730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1608 0.2278 -2.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8358 -0.8946 -3.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7469 3.5223 -0.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4403 3.2293 1.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 3.4226 1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5534 0.9797 0.9511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8906 2.0519 2.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3316 0.4266 2.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7107 -0.2714 -2.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9172 0.2538 -3.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8959 -0.5746 -2.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9718 -2.7911 -2.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4926 -4.9523 -2.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2424 -6.3609 -1.9339 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4632 -5.5290 0.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9678 -3.3209 0.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8411 0.0951 2.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8482 -4.7746 0.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 9 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 26 36 1 0 25 37 1 0 37 38 2 0 37 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 41 44 1 0 44 45 1 0 44 46 1 0 25 47 1 0 23 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 55 56 2 0 22 57 1 0 16 58 1 0 15 10 1 0 42 20 1 0 44 22 1 0 29 24 1 0 31 28 1 0 56 51 1 0 1 59 1 0 1 60 1 0 1 61 1 0 2 62 1 0 2 63 1 0 3 64 1 0 3 65 1 0 4 66 1 0 4 67 1 0 5 68 1 0 5 69 1 0 8 70 1 0 9 71 1 0 11 72 1 0 12 73 1 0 13 74 1 0 14 75 1 0 15 76 1 0 16 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 23 81 1 0 24 82 1 0 26 83 1 0 27 84 1 0 27 85 1 0 28 86 1 0 30 87 1 0 30 88 1 0 35 89 1 0 35 90 1 0 35 91 1 0 36 92 1 0 43 93 1 0 43 94 1 0 43 95 1 0 45 96 1 0 45 97 1 0 45 98 1 0 46 99 1 0 46100 1 0 46101 1 0 47102 1 0 47103 1 0 47104 1 0 52105 1 0 53106 1 0 54107 1 0 55108 1 0 56109 1 0 57110 1 0 58111 1 0 M END

Standard InCHIKey	LRZMCWPHMHOWNG-RDVZGMIZSA-N
Standard InCHI	InChI=1S/C44H53NO13/c1-7-8-11-20-31(48)45-33(26-16-12-9-13-17-26)35(50)40(53)56-28-22-44(54)38(57-39(52)27-18-14-10-15-19-27)36-42(6,37(51)34(49)32(24(28)2)41(44,4)5)29(47)21-30-43(36,23-55-30)58-25(3)46/h9-10,12-19,28-30,33,35-36,38,47,50,54H,7-8,11,20-23H2,1-6H3,(H,45,48)/t28-,29+,30+,33?,35+,36-,38-,42+,43-,44+/m0/s1
SMILES	CCCCCC(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(=O)C(=C2C)C3(C)C)C)OC(=O)C6=CC=CC=C6)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	803.35	Volume:	809.237 ? Van der Waals volume.
Dense:	0.993	LogP:	3.667 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.56 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.173 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	38.0
TPSA:	212.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.105	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.872	Fsp³:	0.545
MCE-18:	157.588 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.659	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.393 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.185	MDCK Permeability:	-4.71
Pgp-inhibitor:	0.005	Pgp-substrate:	0.116
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.82
20% Bioavailability (F20%):	0.62	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.999
Plasma Protein Binding (PPB):	94.779%	Volume Distribution (VD):	0.205
Fu:	4.073% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.205
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.0
BSEP inhibitor:	0.893

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.776	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.877	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.493	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.992 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.495

Half-life (T1/2):

2.039

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.863	Drug-induced Liver Injury (DILI):	0.917
AMES Toxicity:	0.77	Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.862	Skin Sensitization:	0.775
Carcinogencity:	0.264	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.975	Ototoxicity:	0.973
Hematotoxicity:	0.131	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.564
A549 Cytotoxicity:	0.083	Hek293 Cytotoxicity:	0.964
BCF:	0.916 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.912 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.647 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.854 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC327764 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	11803
0.1-0.2	35946
0.2-0.3	2002
0.3-0.4	42
0.4-0.5	18
0.5-0.6	28
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8265	Intermediate Similarity	NPC317882
0.7353	Intermediate Similarity	NPC473300
0.7238	Intermediate Similarity	NPC478329
0.7212	Intermediate Similarity	NPC473400
0.7212	Intermediate Similarity	NPC191193
0.6729	Remote Similarity	NPC603171
0.6486	Remote Similarity	NPC471606
0.6216	Remote Similarity	NPC471754
0.6161	Remote Similarity	NPC487360
0.6161	Remote Similarity	NPC471629
0.6161	Remote Similarity	NPC306001
0.6122	Remote Similarity	NPC197037
0.6122	Remote Similarity	NPC91730
0.6071	Remote Similarity	NPC479183
0.6071	Remote Similarity	NPC324251
0.6071	Remote Similarity	NPC206211
0.6071	Remote Similarity	NPC479181
0.6053	Remote Similarity	NPC275170
0.6018	Remote Similarity	NPC479182
0.6018	Remote Similarity	NPC479180
0.5982	Remote Similarity	NPC453583
0.5929	Remote Similarity	NPC33372
0.5929	Remote Similarity	NPC67246
0.5893	Remote Similarity	NPC321072
0.5893	Remote Similarity	NPC215892
0.5893	Remote Similarity	NPC242662
0.5893	Remote Similarity	NPC102167
0.5893	Remote Similarity	NPC488127
0.5841	Remote Similarity	NPC471623
0.5841	Remote Similarity	NPC208553
0.5841	Remote Similarity	NPC181964
0.5841	Remote Similarity	NPC307628
0.5804	Remote Similarity	NPC36607
0.5794	Remote Similarity	NPC603140
0.575	Remote Similarity	NPC472392
0.5726	Remote Similarity	NPC486061
0.5726	Remote Similarity	NPC486060
0.5678	Remote Similarity	NPC487361
0.5588	Remote Similarity	NPC605573
0.5478	Remote Similarity	NPC327699
0.5403	Remote Similarity	NPC479173
0.5192	Remote Similarity	NPC229545
0.5192	Remote Similarity	NPC248265
0.5192	Remote Similarity	NPC134685
0.5094	Remote Similarity	NPC155329
0.5094	Remote Similarity	NPC114357
0.5085	Remote Similarity	NPC478328
0.5042	Remote Similarity	NPC473558

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC327764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3444
0.1-0.2	5577
0.2-0.3	116
0.3-0.4	0
0.4-0.5	5
0.5-0.6	7
0.6-0.7	0
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
0.5893	Remote Similarity	NPD8360	Approved
0.5893	Remote Similarity	NPD8361	Phase 4
0.5841	Remote Similarity	NPD8485	Phase 4
0.525	Remote Similarity	NPD8486	Phase 1
0.5126	Remote Similarity	NPD8368	Phase 2
0.5085	Remote Similarity	NPD8424	Phase 3
0.5042	Remote Similarity	NPD8435	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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